All Episodes

September 19, 2025 48 mins

Send us a text

Our first eviction experience turned into a year-long saga of legal hurdles, thousands in lost revenue, and unexpected emotional challenges. We navigate the complex process of evicting non-paying tenants from our commercial property in Chicago while balancing business decisions with human impact.

• Notice requirements for tenant termination in Chicago (120 days for tenants who've lived there over 3 years)
• Impact of problem tenants on other units and building conditions
• Timeline from notice to actual eviction spanning nearly 12 months
• Legal procedures including court dates, default judgments, and sheriff scheduling
• Importance of not accepting rent after termination notice
• Financial impact: over $10,000 in losses from legal fees and missed rent
• Emotional reality of eviction day with six sheriff officers and social workers
• Cash-for-keys as a potentially better alternative to formal eviction
• Location matters - eviction laws vary significantly between different states and counties
• Single-unit rentals carry higher risk compared to multi-unit properties

If you're considering real estate investing, understand that evictions are sometimes unavoidable but should be your last resort. The financial and emotional cost makes cash-for-keys deals worth considering before entering the lengthy court process.


Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Welcome back to another episode of the Real Life
Investing Podcast with Jasonand Rachel Wagner.
Rachel, we're celebrating 5,000downloads.

Speaker 2 (00:07):
Yeah, I know it's amazing.
It's pretty awesome, yeah, andI will tell you, the struggle
has been real to actually recordanything new.

Speaker 1 (00:16):
Yeah, yeah, why?
Why, as of recently?
First off, the summer stinks.

Speaker 2 (00:22):
Yeah, yeah.

Speaker 1 (00:22):
The summer really stinks.

Speaker 2 (00:23):
Yeah, yeah, the summer really stinks, yeah, yeah
, we.
You may even be able to hear alittle bit of the struggle in
the background of the reality ofwhere we're at.
I mean, we welcomed a new babyboy in May and made the decision
to embark on homeschooling thisfall.
Embark on homeschooling thisfall, and so what we're, you

(00:44):
know, not realizing, because weobviously knew this was going to
be the case.
But discovering is.
Time is flying by and it's notour own, and finding the time to
have a quiet space and do arecording is is a very, very new
struggle.

Speaker 1 (01:00):
Yeah, it's a very real, real struggle right now.

Speaker 2 (01:03):
But we're here and we're doing it.

Speaker 1 (01:04):
Yeah, you know, in the summer you know the kids are
home and you know they justthey're always here.

Speaker 2 (01:10):
They're always here and now.
That remains true.

Speaker 1 (01:13):
And that remains true because we decided For the
foreseeable future.
Yeah, because we decided tohomeschool Scarlett.

Speaker 2 (01:18):
Yeah, which has been amazing.
I'm really glad that we'redoing that.

Speaker 1 (01:27):
I think that was the right decision.
Yeah, oh, absolutely,absolutely.
Yeah, no, it's going to beamazing.

Speaker 2 (01:29):
That's our life Well, and the beautiful thing is it
kind of leads into some of whatwe're talking about.
As part of the homeschool,scarlett gets to shadow you
during appointments where thatmakes sense, and so you've been
able to have some newconversations with her about
real estate and what it means toown a property, what it means
to rent a property, and wehaven't gone into the details of
what we're going to talk abouttoday but at some point it'll be

(01:52):
a great lesson for her too.

Speaker 1 (01:53):
Yeah, because we recently had the tenants move
out of our last house or asingle family home that we had
in Jefferson Park.
Tenants lived there for twoyears and I brought Scarlett
over to see how the house lookedafter the tenants moved out.
And kind of a fun experience.
Because she's like oh, dad,they didn't really take care of

(02:16):
it here and I'm like, well, youknow, when you move out of a
house it's still going to bepretty messy.
And and then you do start toidentify things that are like oh
yeah, you know there's there'sa lot of burnt out light bulbs
and you know it does look alittle messy over there.

Speaker 2 (02:29):
Yeah, I asked her how it went.

Speaker 1 (02:30):
There's like permanent stains on some things.
And you know, I ultimately toldher.
I said, you know, at the end ofthe day, scarlett, everything
is fixable, and that's the coolpart.
Part of this next exercise withher is that she did see it when
they moved out and then nowwe've just recently kind of
fixed everything and I do wantto bring her back before the new

(02:53):
tenants move in so that she cankind of see the whole
transformation of like oh, myhouse looks like, or this house
looks like what it used to looklike when I lived here.
So it'll be a kind of a coolbefore and after.

Speaker 2 (03:03):
Yeah.

Speaker 1 (03:04):
For the kids.

Speaker 2 (03:05):
Yeah, it's so cool to like hear what a kid's
perspective is on on some of thestuff, cause I remember asking
her how it went and she's likeit was so messy, it was just so
funny, like they had just movedout.

Speaker 1 (03:16):
Yeah so yeah, it is what it is.
You know, at the end of the day, a tenant is not going to treat
your property the way that youwould treat your property, and
so the expectation should not bethat they're going to treat it
the same way that you would.

Speaker 2 (03:30):
Yep, and it's baked into your cost.
Right yeah, your budget.

Speaker 1 (03:34):
Yeah, exactly, all right.
Well, that leads to speaking oftenants.
It leads into our new topic,which is talking about our
experience with our firsteviction, where we finally saw
it the distance we went fromgiving a notice.
This was on the commercialbuilding that we bought.
We actually had an episodewhere we talked about this

(03:55):
commercial building, our firstcommercial apartment, and that
was actually a pretty goodepisode.
There's a lot that's in our topfive download list of people
being interested in how wepurchased our commercial
property.
Well, as we've owned this oneover the last or a little bit
over a year, about a year and ahalf we had one unit that was

(04:17):
kind of remaining.
That was really gross, notrenovated, full of cockroaches,
like a really bad infestationthere, but people were living
there and people were hoardersand they had lived in the
building for, I believe, sevenyears and it looked like they
just moved in because they stillhad boxes everywhere and it was

(04:40):
just really gross.

Speaker 2 (04:42):
And were they on a lease or were they living month
to month?

Speaker 1 (04:44):
They were technically on a month to month agreement.
And so when we acquired thebuilding, we acquired the
tenants and that was kind oflike hey, this is the problem
unit.
They were still paying.
You know, their rent was $950.
It's a two bedroom, one bath inPorridge Park, which is very
low.
Yeah, very low Also, butprobably appropriate for the
condition of the unit, like itwas gross and it's not renovated

(05:08):
at all.
So I made the decision toterminate their lease and I gave
them, because they had lived inthe property more than three
years, you got to give them 120day notice, so I gave them a
four month notice.
So on July 31st of 2024, I gavethem a notice that they need to
move out by the end of November.
So November 30th.

Speaker 2 (05:29):
So just curious, since you made the point that
they had lived there longer thanthree years, they got 120 day
notice.
What's the notice if it's under120 days?
60 days, excuse me, yeah.

Speaker 1 (05:38):
Yeah, so in Chicago is actually Lori Lightfoot that
put in this new ordinance, atleast for the amount of notice
that you need to give somebody.
So if a tenant has lived in theproperty for more than three
years and you are going toincrease their rent, put them on
a new lease or terminate theirlease, they need 120 day notice.
So that's four months.

(06:00):
Yeah, it's a lot Four months tolet somebody know, and if
they've only lived there forless than three years, it's just
60 days.
Okay, so you have to abide bythat.
And so I gave them, you know,the four-month notice, and they
agreed.
They said, okay, you know, weunderstand, you know the unit's
in really bad shape and you knowit would just be best if we got

(06:23):
out of here too.

Speaker 2 (06:28):
So they were in agreement.

Speaker 1 (06:29):
So your notice wasn't .
Your rent is going up.
Your notice is you need tovacate.
I wanted to terminate theirlease because that unit needed
to be addressed.
It's an infestation ofcockroaches and I can't address
the unit when it looks the wayit is.
Yeah, you know it's not cleanand whatsoever.
The air that you would breathein that unit was like hot, gross
, nasty air.

(06:49):
This is not a place for humansto be living.
Honestly, it was.
It was that it was that bad.
When we did the inspection onthe property, the inspector had
to wear an N95 in there theentire time.
And I'm like, dude, I'm not,I'm not going to sit in that
unit while you're inspectingthis thing.
Why don't you go in there anddo your thing and come back out

(07:10):
and let me know how it goes?
And he's like.
I could feel it through the N95that my respiratory system was
like getting affected.

Speaker 2 (07:23):
But didn't you have somebody who went through the
unit who said that there's aparticular smell that comes from
like a hoarder house?

Speaker 1 (07:29):
Yeah, it was actually one of the, so the pest control
guy, when he first came and Imet him there the first time and
he's like, oh, hoarder smell.
I was like what they come witha smell.
He's like, oh yeah.

Speaker 2 (07:42):
Yeah, it's a distinct , it's a distinct, just nasty
smell.
Yeah, and you got to thinkabout how that's impacting the
other tenants in the building.
Right, like with theinfestation of cockroaches,
there's going to be someoverspill into other units, and
that's what was happening.
It impacts other people'sexperience, yeah.

Speaker 1 (08:00):
The unit above.
We were trying to lease it andas I was doing some of the
showings, I was like, dude, I'mfinding roaches in this.
Like the roaches, it's a vacantunit right now and it looks
really good, but there's roachesin the cabinets and there's
roaches that are crawling on thefloor and it's coming directly

(08:21):
below from this unit.
And so I had to.
You know, over the course oftime we just had a regular pest
service that would come in andyou know they would treat just
that unit, because I would askall the tenants if they were
seeing any activity in theirother units.
It was only this ground zerounit that was really the big
problem.
So, anyways, you know weaddressed it and actively tried

(08:44):
to, you know, help it.
So they have a notice to moveout.
And November 30th comes andthey're like, yeah, we're not,
we're not going anywhere.
And what happened a couplemonths before that was that the
head of household so there'sreally three people in this unit
, two that are in their 60s andthen their older son, who's

(09:06):
probably in his 40s, livingtogether.
And what happened to the headof household, who was the guy
that I was talking to about allof this, was that he landed in a
nursing home because he had astroke.
And here's the interesting parthe actually puts his stroke on
the COVID vaccine, which he toldme that, and he's like it was

(09:30):
the COVID vaccine that put me inthis hospital and now I've had
a stroke and then it's just, henever got better.
Like they never ended upreleasing him.
He's still there now, which iskind of crazy.

Speaker 2 (09:44):
Well, and has made this process like super
difficult, right Like you issuedthat notice back in July, and
when did that whole thing happen?
Because that person's not evenliving there.

Speaker 1 (09:54):
No, he's not living there.
All of the stuff is there Rightand the other two people were
living there and the other twopeople were living there.
But like the person, yeah, onthe lease.

Speaker 2 (10:00):
Isn't living there.
And yeah, it's complicated.

Speaker 1 (10:11):
Yeah, on the lease, isn't living there and yeah,
it's complicated.
Yeah, yeah, exactly, and so youknow it's made it very
difficult.
Situation where I've got thehead of household in a nursing
home.
His wife and son are living inthe apartment not taking care of
it.
His wife is disabled, doesn'tmove around very good.
I know his son has a number ofissues himself as well and
actually we're just we're justdealing with like handicapped

(10:34):
people, you know, the wholefamily at this point is is just
handicapped.

Speaker 2 (10:38):
Yeah.

Speaker 1 (10:40):
And so it makes it really challenging.
And so I did the honestly I,you know.
So I did the best that I could.
I told them I'm like, hey, Ican help you look for other
apartments and I would activelylook on what was available on
the rental market and I wouldsend them opportunities.
And then they were just like no, it needs to be first floor, it
needs to be under.

(11:00):
We're spending $950 now.
We'd actually like to spendsomething that's $800.
And I'm just like dude, youcan't.
He's like I need to have a twobedroom and I'm just like dude,
you, you just can't get that youknow.
So we have a problem of theycan't just go find something
else that suits their needs.
I'm actively trying to helpthem and it's just not quite

(11:22):
working.

Speaker 2 (11:23):
So this timeframe was like between the time that you
gave them notice and then whenthe new rent was going to
increase.
So the during that 120 dayperiod.

Speaker 1 (11:32):
Well, I didn't really .
I mean, I gave them a, like anincrease of rent notice like,
hey, here's what you could do ifyou want to continue to stay
here, but we wanted thetermination.

Speaker 2 (11:42):
Okay, that's right.
You just said we wanted thetermination.
Okay, that's right.

Speaker 1 (11:45):
You just said we wanted the termination yeah,
okay, because the increased rentwasn't going to make sense for
them.

Speaker 2 (11:49):
Okay, so you give them the notice You're trying to
help them find a place.

Speaker 1 (11:54):
And then you get to the point where they're supposed
to vacate and they don't Right.
And so, from here, this iswhere we file a suit of you know
, now we need to get this intothe court to start the eviction
process.

Speaker 2 (12:07):
And did they pay?
Continue to pay their month tomonth rate.

Speaker 1 (12:18):
So when you go to terminate somebody's lease and
they are still there after yourtimeframe and they're in a month
to month, you cannot accept newrent.
He wanted to pay me hisDecember rent.
He wanted to pay me that 950.
But I said I'm not accepting it.

Speaker 2 (12:31):
Because you want the unit vacated, because I want the
unit vacated because this is abig problem within this
apartment building.
Yeah, and that's a toughdecision and a good, I think,
distinction on the rules is hadyou accepted that rent, would
that have made your 120 daynotice null and void, because
you would have essentiallyentered into a new month to

(12:52):
month agreement with them?
Oh, exactly, yes, so if youwould have, accepted payment for
rent at the end of that 120days, you then would have had to
have start that 120 day processall over again, because you've
got this verbal, so to speak,month to month written agreement
.

Speaker 1 (13:07):
Yes, yeah, and sometimes a tenant will send it
to you electronically by Zelleand you're supposed to
immediately send that back.

Speaker 2 (13:15):
Is there a time frame for what you have to do that?

Speaker 1 (13:18):
Like immediately yeah , yeah, yeah.

Speaker 2 (13:21):
Okay, so he wanted to pay you rent.

Speaker 1 (13:37):
You said, no, you need to vacate, and what they
say.
But we've got this.
Like you know, I've got myhealth problems that are going
on and you know my son can't dothis by himself and you know my
wife's not able to do this andyou know we don't have a lot of
money to, you know, to hiremovers or anything like that and
we can't find a new place.
And they told me, well, serveus the eviction paperwork,

(14:01):
because then we can go and takethat to social services
paperwork, because then we cango and take that to social
services or, like you know, Imight be able to find a place
and you know, and they want tosee that I've been served, so
that can help us look for aplace.
I said okay, I'll work on that,no problem.
So I contact the attorney andwe file the complaint on
December 16th and it's kind offunny.

(14:22):
So as I you know, I gotreferred to this attorney.
I probably wouldn't refer themto other people.
It wasn't that good ofexperience.
There was a lot of fumbles thathappened along the way.
Like this is just the realityof it, right, and not to talk
bad about anybody, but it's just.
It wasn't.
Eviction this eviction processis not going to be smooth.

(14:42):
You just have to plan that thisis going to be a very long time
.
Eviction this eviction processis not going to be smooth.
You just have to plan that thisis going to be a very long time
.
It's going to be a frustratingtime.

Speaker 2 (14:53):
It does not help that if you fumble some things along
the way either.
Right, so Well, and there wassome interesting discussion with
the attorney throughout theprocess of like frustration on
our end, a lack of urgency, andthe response that was given a
couple of times was like look,you don't want to overly push
the sheriff's department or thecourt system, because then
they're just going to delay youmore on purpose because they
don't want to be pushed.

(15:14):
So you got to kind of likecoddle them and be really nice
and it was kind of like this isridiculous, like who knows if
that was true or accurate, butthat was the communication that
was coming from the attorney islike look.
I've done this so many times.
I know we've got to kind ofhandle this with you know
delicacy and it's like, well, inthe meantime we're not getting

(15:36):
paid.

Speaker 1 (15:37):
And the unit continues to degrade.
Everybody's going to have thatsame mindset, right?
It's like this is gettingridiculous.
It's taking too long.
Mindset right, it's like thisis getting ridiculous.
It's taking too long.
I mean, we haven't gotten tothe details of why we needed
them to push, because there wasliterally some oversight by the
sheriff department where we wereon the book scheduled for to be
evicted the next day and thenall of a sudden we weren't and

(15:59):
we were removed, and then all ofa sudden they said that our
eviction order was expired.
I'm like how the hell do wehave an expired eviction order
when it's taken this long, likeI didn't even know these things
expire.

Speaker 2 (16:11):
Okay, so let's back up.
So you filed the evictionpaperwork.

Speaker 1 (16:15):
Right.
So we filed the evictionpaperwork and that was on
December 31st.
Okay.
So actually which was funny wefiled it on the 16th and then I
noticed that there were errors.
So then they had to file itagain, and then that was on the
31st of December.
Okay, so then you get set upwith a new court date or with

(16:36):
your first court date, andthat's like two months away from
when you file.
So that was on February 10th.
So we filed that, the second,the second complaint, because
the first one was wrong.
We filed the second complainton December 31st.
We didn't get a court dateuntil February 10th.
Well, the 10th didn't show up,okay.
So then you get into acontinuance and you know, oh,

(16:59):
the judge is like well, maybethey can come to the next one,
right?
So then you have your secondcourt date, and that was on
February 25th, so not that muchlonger, and the tenants didn't
show up to that either.
So here I was thinking like, oh, they don't show up.
And then we're told that theeviction becomes enforceable
after seven days from thatsecond court date.

(17:20):
And so here I'm thinking, oh,we're all of a sudden going to
get like approval on thiseviction order, and it's only
been a couple months.
Yeah, three months, like.
That's like that sounds prettygood.
Yeah, great, that's that thatsounds pretty good yeah, still
three months no payment, thoughbut they have this thing where
it's like the tenants can appealwithin the next seven days from

(17:42):
that eviction order or fromthat second court date, and so
let's see what do I write here.
So the eviction is enforceableafter seven days If not gone by.
Oh, okay, yeah, the eviction isenforceable by seven days.
If the tenants didn't move outby March 5th, we can place the

(18:03):
order with the sheriff.
And we were actually awarded ajudgment on them.
This was a default judgment ofabout $3,300, $3,400.

Speaker 2 (18:14):
And what does that mean?

Speaker 1 (18:16):
So eventually, like they actually just kind of
calculate, like because in theprocess he was like, okay, how
much rent did they actually oweyou?
Because they start to look at,okay, when did the lease end,
and then how many months havethey been there for?
And so they automatically willput a judgment on the past due
rent.
Right, because they're still inthe property.

(18:38):
And from what I've learned isthat you can try to go after and
, you know, put a judgment onthem and garnish their wages and
, you know, try to get some ofthis back due rent.
But I don't really have a lot ofsuccess stories of people doing
that and I eventually just kindof dropped.

(19:00):
That, you know, is like Ididn't care about you know,
getting the rent that was due.
They already had a low amount.
You know, getting the the rentthat was due, they already had a
low amount and I was willing to.
Just if we could just move thisalong or get them to move out,
I'm totally okay with not havingyou know them paying me the
past due rent and just give mepossession back.

Speaker 2 (19:21):
It seems very reasonable oh yeah, that's, very
fair all right.

Speaker 1 (19:25):
So so they, they tell me hey, if on March 5th if
they're still living there,let's see March 5th, if they're
still living there, I can expectseven to eight weeks for the
sheriff.
So if on March 5th they'restill living there, then we
would have an enforceableeviction and then we'd have to
put it in with the sheriff, andthat's going to take another
seven to eight weeks Because thesheriff is backlogged on all

(19:49):
this stuff.
So within that seven day windowafter that second court date,
the tenant actually got in touchwith an attorney and they filed
a motion to vacate the defaultjudgment.
So now we get like a curveballthrown at us where, yeah, just

(20:14):
because the tenants didn't showup to the court date, but they
did get in touch with somebody,with an attorney, to help them
through this, and so thatattorney was able to file a
motion to get rid of the defaultjudgment, which led us into
negotiation of hey, we'll dropthe judgment if you move out by
a certain date.
And so the tenants needed moretime to move out, and so we

(20:39):
agreed that the tenants wouldmove out by May 15th, and this
was in.
This was March 24th at the timewhen we made this agreement,
you still following Mm-hmm?
Okay, so then from there we weregoing to say, okay, if they
don't move out by May 15th, it'sgoing to be another four to

(21:02):
eight weeks for us to getpossession of the unit back and
that's going to place us in July.
Okay, so then May 15th comesand they don't move out, and so

(21:22):
we finally get the eviction inthe sheriff queue and that
doesn't happen until, for somereason, that doesn't happen
until June 2nd, and then wefinally, on July 1st, we get
scheduled to evict.
That's going to be the day,july 1st.
So, as what I was expecting islike, okay, it's going to land
in July, we're going to havethis eviction happen.
And so when you get notifiedthat, hey, you're finally on the

(21:43):
schedule, the sheriff is goingto come, they notify you like
the business day before it'sgoing to happen and you have to
have somebody be there between afour hour window, and so you
have to drop everything thatyou're doing and meet the
sheriff there.
And if you don't approach thesheriff within five minutes of

(22:04):
them pulling up, apparently youcould miss it.
And so, super important to makesure that you have somebody
there.
And so I cleared my scheduleand I was like all right, I'm
going to go, we're going to godo this.
You know the sheriff's going topull these guys out.
You know, it's kind of as whatwe expected on the timeline and
we're going to get possessionback.
So then, literally the night of, we just found out about it

(22:29):
during the, during the day, andthen later that night we find
out that oh no, our evictionorder expired and we're not on
the list anymore.
We're canceled.

Speaker 2 (22:40):
Yeah, expired from the court.

Speaker 1 (22:42):
right, yeah, yeah, the original one and I'm like
what the fuck?

Speaker 2 (22:46):
You had no control over anyway.
No.

Speaker 1 (22:48):
And I'm like what the fuck?
Which you had no control overanyway, no.
And I was like how do you evenhave an expired eviction order,
like I didn't know that thesethings expire?
And if you're in a county thattakes so long to go through this
process, why would theexpiration date be so short?

Speaker 2 (23:01):
Right.
How would it even ever work,like if the court gives you six
weeks, for example, and thesheriff needs seven to eight?
You're always going to expire.

Speaker 1 (23:10):
It's just like ridiculous things that kept
happening Like this was insane.

Speaker 2 (23:15):
Yeah, cook County.

Speaker 1 (23:18):
And so it takes us a while to like figure out, like
what the hell happened.

Speaker 2 (23:22):
And at this point you're already at a year from
having given them notice tovacate in four months.

Speaker 1 (23:27):
At this point, I am at that year, yeah, year mark of
when I given them notice tovacate in four months.
At this point, I am at thatyear, yeah, year mark of when I
gave them notice.

Speaker 2 (23:31):
four months notice, yeah, so eight months of not
being paid, 12 months of justdealing with the communication
and the process of this ingeneral.

Speaker 1 (23:39):
Yeah, Yep, Yep, so then.
So then I get kind offrustrated with the attorney.
I'm like how the hell does thishappen?
And he's like, well, itshouldn't have expired because
we actually filed a secondeviction order and they should
have been able tocross-reference and look that
there was a second one that wasapproved that has a longer

(24:01):
expiration date.

Speaker 2 (24:03):
Yeah, and I remember this time because this is when
there was like a lot ofconversations happening of like
trying to get in touch with thesheriff, the sheriff saying one
thing, the attorney sayingsomething different, something
else happening in actuality.
It was just like nobody knewwhat the hell was going on, like
when we were like trying tofigure out just in communication
, like what's happening withthis eviction.
I have no idea, I don't knowwhat's going on with this
eviction.
I have no idea it's supposed tohappen.

Speaker 1 (24:34):
Now don't know, we might have to go back to court
like just a shit show.
It was a shit show.
And then at the same time, I'vegot a partner on this right.
So you know, and is it okay ifI say who he is or no?
okay, no, I won't say it, butbless his heart because he's
just like you know, I'm gettinga little impatient on this and
I'm like I know I am too andhe's like, well, what's stopping
us from just you know sittingoutside one night and watching
him walk outside of the unit andthen just going and you know

(24:54):
changing the locks, and I'm likeyou know that, I think, is
called a self eviction and isactually punishable as, like a
felony.
Yeah, so I don't think that's agood idea.

Speaker 2 (25:08):
He's like felony yeah , so I don't think that's a good
idea.
He's like what yeah?
Because from the businessstandpoint it is wild.
It is wild that you can haveownership of a property yet have
zero control.
Like you have had zero controlover this unit for eight months
at this point.
Arguably Right.
No payment, no control over theunit.

(25:30):
Your hands are tied and you'restill obligated to pay your
mortgage, right?
So this is like a little bit ofthe risk, not a little bit.
This is the risk side of owningproperties and renting them out
because you're still on the hookto make your payments, but
you're not receiving payment andthere's nobody helping you
speed this along.

Speaker 1 (25:48):
Nobody is helping you , and if you?

Speaker 2 (25:49):
aren't like aware of what you can and can't do, you
could make a lot of misstepsalong the way.

Speaker 1 (25:55):
Well, and you know, and here's the thing is that we
filed this eviction right awaybecause they were supposed to
move out November 30th, and thenwe filed it the next month, so
technically right away.
But imagine when you're in theposition of you're dealing with

(26:15):
a tenant who just stopped payingyou and they're telling you hey
, I'll get it to you next month,I'll get it to you next week,
next week, next week, all of asudden that turns into three
months, sudden that turns intothree months.
So if you've got a scenariowhere you're like dude, they're
three months behind, they keeptelling me they're going to get
it, I think I'm finally going togo ahead and do the eviction

(26:40):
paperwork.
Well then, you just stackedanother four to nine months on
top of the three months thatyou're late.

Speaker 2 (26:47):
Right, and you want to pay attention to that too,
because, let's just say,somebody's you know lived there
for two and a half years orsomething and they've got a few
more months left on their lease,like the amount of notice
you're required to give themthen, too, for eviction.
Is that longer, or is that onlyif you're ordering them to
vacate?

Speaker 1 (27:05):
No, the notice is the same.

Speaker 2 (27:06):
Okay, the notice is the same, so even if they ticked
over to living there threeyears, there's nothing that
would change in that non-paymentprocess.

Speaker 1 (27:13):
No, because they're still behind on the rent.

Speaker 2 (27:15):
Okay.

Speaker 1 (27:15):
Right.
So really what you need to do isthat when somebody stops paying
you rent and if they don't payyou rent by the 5th, like it's
late on the 6th, and if you'vegot a problem tenant and like

(27:46):
you kind of know that on the 6thyou should be serving them a
five day notice to pay rent andthat five day notice is ended
and they were still occupyingthe unit, right, so we were able
to file the complaint rightaway.

(28:08):
You know, you need to be veryproactive with issuing this
five-day notice and that needsto be served to them in person
and it needs to be given tosomebody that is, I believe,
above 13 years of age, thatlives in the unit.
So you can get it doesn't haveto be the adult household, it
just needs to be somebody thatis above 13 years of age.
I remember when I was in theproperty management class at
Chicago Association of Realtorsthat I took the guy that was
doing it his name was Taff Westand like legendary in Chicago

(28:31):
and he would go with a smilingface and he would go and like
knock on the door and say a kidwould like open the door and
he'd be, like hey, buddy, andyou know he wouldn't tell him
why he's there.
He'd be like hey, buddy, how areyou?
Oh, good, good, you know hewould ask, you know, if his
parents were home and be, like,yeah, and remind me again how

(28:54):
old are you.
He'd be like 14.
Perfect, here can you give thisto your mom and dad, right?
So, yeah, so you actually haveto physically serve it, that
five-day notice to people, okay,so then, yeah, that complaint
is then issued, and so you justhave to like, keep that stuff in
mind.

Speaker 2 (29:13):
So okay, so let's go back to our timeline.
So it was supposed to be in thesheriff's schedule, but then we
got canceled and we don'treally know why.
But you do a new court dateright Cause it expired.

Speaker 1 (29:24):
Yeah.
So then all of a sudden we'respending basically the whole
month of July trying to figureout what the hell happened.

Speaker 2 (29:32):
Yeah, that was that.
Nobody knew what was going on.

Speaker 1 (29:34):
Nobody knew what was going on and I have this fear of
like dude.
We just started back at thebeginning of the line.
And now we got to go back towhere we were in December.
Yeah, like that was.

(30:01):
My fear is that all of a suddenwe were.
We were totally like screwedhere.
Yeah, was approved with alonger termination date, and so
the sheriff just needed to lookat that other order and they
didn't.
And I'm like, all right, whydon't you call them and tell
them you know what happened andthat it was an oversight?
And he's like, well, this iskind of going back to where you
were talking about earlier,where it's like, well, we can't

(30:21):
really push them too much,because then they may not like
us, and then it's just going tomake things more difficult.
And I'm like, dude, we were onthe schedule, we were supposed
to be, this was supposed to bedone the other day and all of a
sudden we're not, and it's beenlike another month and we have
no idea what's happening.
And it's just chaos in my head.

(30:42):
It's chaos in my head becauseI'm like, dude, this is never
going to end.
And so we, ultimately, wefinally were able to kind of
push the guy a little bit and so, but he had to go back to court
.
I don't understand why, but hehad to go back to court to file
a motion for extension.
He came out of that court date,and that was on August 12th.
He came out of that court date.

(31:02):
He's like, hey, there wasactually a new judge and I was
like what does that matter?
And so they issued a seven-dayextension on this.
So, like this new judge issuedanother seven days for the
tenant to realize that like hey,you're being evicted and like
it's now coming like imminent orsomething.
And so then seven days goes by,and then the order extending

(31:26):
eviction.
Let's see what did I writethere.
Okay, so then we got the orderextending the eviction until
December 17th of 2025.
So now, all of a sudden we'vegot our expiration date is now
in December.
I'm like, okay, it's going tohappen this year, yeah.

Speaker 2 (31:42):
And again that's valid to get on the sheriff's
schedule.
You've got this window now toschedule with the sheriff to
actually do the eviction.

Speaker 1 (31:50):
Yeah, and then at the end of August we get a notice
that, hey, it's probably goingto happen within the next two
weeks, and then two weeks goesby, two weeks for the sheriff
and then two weeks goes by andwe don't.
It doesn't happen.
Like on the 14th day I'm asking, hey, it didn't happen within
this next two weeks that yousaid what's happening.
So then we, finally the guy is.

(32:15):
The guy starts asking theattorney, starts asking his
other partners.
He's like, yeah, I think wemight have to like maybe sue the
sheriff's department for notdoing their job.
And like he started asking hiscolleagues on if he should do
that.
And I'm just like this is adisaster man.
What a nightmare.
Yeah, All of a sudden we're notjust suing the tenant Now,

(32:36):
we're suing the sheriff to dotheir job.

Speaker 2 (32:39):
Yeah, which just sounds like an impossible feat.

Speaker 1 (32:42):
So within this like exploratory phase of, are we
going to sue the sheriff?
We then get noticed that theeviction is going to happen on
September 15.
And so that was on Monday thispast week and we got notice of
it on Friday that it was goingto happen On Saturday.
Here's an interesting part Ihaven't heard from the tenant in
a while, and the tenantmessages me this very long

(33:05):
thread about their personalsituation.
I won't go into it, but withinthis very long thread that he's
talking about his family membersand the backstabbing that's
happening and just theirproblems and whatnot.
He says can you come over andfix the pilot light on the hot
water heater because it went out?
He says can you come over and,like, fix the pilot light on the
hot water heater Because itwent out?

(33:25):
And and my my response is justI go and I I messaged my
handyman to go check out thepilot light.
And then I just text him backand I say the pilot light is on
because I know on Monday he'sgoing to get evicted.
Then the eviction day happens,right, and so I have to be there
between 8 am and 12.
And the sheriff's going to showup at some point, right?

(33:47):
So I have to meet them thereand you only have five minutes
to approach them, so you got tomake sure you're not, you know
you don't miss them.
And that, like I got thesethings that are happening in my
head because all of a sudden Iget to the, I get to the
building, they're likeconstruction going on and one of
the we got a corner buildingand in one of the corners, one
of the streets, there's roadworkgoing on.
I'm like whoa, this is kind of aproblem.

(34:09):
And then so I park on the onestreet, but I'm kind of like
hidden by the building and thenI'm sitting there, I'm waiting.
I'm like boy, it's nine o'clock930.
I'm like, did I miss?
Did I miss the sheriff?
Like you know, I'm sittingthere, I'm reading a book and
I'm just like looking up anddown and I'm just like, dude, I
hope I didn't miss the sheriff,you know, because I can't see
them and I hope they don't.

(34:32):
Like you know, they should beeasily identifiable, but I'm not
identifiable, and so I juststart going through this like
psychological craziness in myhead of like, oh my.
God, I'm going to miss this.

Speaker 2 (34:40):
I'm going to miss this because they don't call you
.
Just have to meet them whateverthat means.

Speaker 1 (34:42):
I found out that they ended up calling the attorney.
The attorney sent me a messagesaying that they were coming
soon.
So that was good, but I didn'tknow that that was going to
happen.
So again, I'm just like playingthese games in my head of like
dude, I thought I saw a whitecar and it had like a sticker on
it.
I'm like, was that the sheriff?
Like, no, I obvious what asheriff vehicle is.
And I'm like, but I did seethat van that had the sticker on

(35:04):
it that said something aboutthe city.
And I'm like, did I miss it?
And so it's just crazy what'shappening here.
And eventually, all right.
So then they pull up and I'mlike, oh, that's them.
Like very obvious, these aresheriff squad cars.
I go and approach and there aresix sheriffs that come up to me

(35:25):
and one of them is the mainperson leading the whole thing
and she's like she pulls me overand she's like, hey, just so
you know you're, you're beingvideo recorded.
What are we doing today?
I said we're evicting from thisone unit and she says, okay,
and who are you?
I said I'm the owner.
And she says, okay, you'regoing to have to open the foyer

(35:47):
door for us and if the tenantdoesn't open up the unit door,
we are going to break down thedoor.
I said, well, I got keys andshe's like, yeah, but we're
going to break down the door.
I was like, oh man.
And so the attorney told methat, like this could be a thing
that happens, and so I did havesomebody that was on standby
that I could call and like, hey,if I need to fix the door, can
you be available?
Well, so they go into the unit,they knock on the door and they

(36:11):
got like guns drawn, like oneguy has it out of his holster.

Speaker 2 (36:16):
Because they don't know if the person on the other
side is going to be hostile.

Speaker 1 (36:19):
Right, they have no idea.
Yeah, and so then?

Speaker 2 (36:21):
There was somebody else.
There too, there was a socialworker, yeah.

Speaker 1 (36:25):
There were two social worker girls that were there.
One of them was wearing likepajama pants.
I was like this is weird,irrelevant detail.
I didn't know what she was.
She was like and she waswearing a bulletproof vest, but
it didn't look like a normalbulletproof vest.
It just looked like a regular,like like a Girl Scout vest,

(36:47):
like that's what it looked like,and then she was wearing a
pajama.

Speaker 2 (36:50):
Are you sure it was a bulletproof vest?

Speaker 1 (36:52):
It had to have been because the two girls were
wearing the same one.
Okay, yeah.

Speaker 2 (36:56):
Well, you sure it wasn't just like an identifiable
vest.

Speaker 1 (36:59):
No, it was just black .
Oh, it was just black, and itlooked like a little bit heavy,
but not like police officerheavy, you know.
And again, one of them was justwearing pajama pants and I was
just like, are you guys withthem or what's going on here?
And so, and she told me, andshe said, yeah, you know, I'm a
social worker.
I said okay, cool.
And so I watched them go intothe unit and it takes them about

(37:20):
I don't know a half hour totalk to the tenant and basically
what happens is that they pullthe tenant out and the eviction
is complete.
And so they come up to me andthey say, hey, jason, come over
here real quick.
And they go to the tenant andthey're like, hey, do you
recognize this man?
And he says yes, and he said,ok, jason, the eviction is
complete, you're going to haveto give them an opportunity to

(37:42):
come get their stuff, becausethey don't take their stuff.
He just came out of the unitholding a grocery bag and the
clothes on his back.
That was about it.
And they said, ok, we're donehere, so we'll see you later.
And so all six sheriffs walkaway and the social workers are
like kind of off, like it lookslike they're walking away too,

(38:04):
and so then it's just me and thetenant like looking at each
other face to face.
I'm like, boy, this is awkward.
I said do you have somewhere togo?
And he's like, oh.
I'm like oh.
I said okay, well, here's whatyou got to do.
I said call my attorney and,like you know, work out a date
to come and get all of yourbelongings.
I said you want your belongings, right?
He's like, yeah.
I said, okay, well, make sureyou call them within the next

(38:27):
seven days.
I said okay, so make sure youcall them within the next seven
days and so you can arrange fora time to come get all your
stuff.
And then I go and change thelocks and I lock the foyer door
and I'm working on the unit door.
I'm like you can see rightoutside because there's a window
there and the guy is justhanging out, the tenant's just
hanging out right on the frontstep, and I'm just like, and I'm

(38:49):
working on the door, and thenhe ends up like mouthing to me.
He's like, hey, can I come inand use the bathroom?
And I'm just like no, like no,no, you can't come in and use
the bathroom.

Speaker 2 (39:02):
Like I just had to forcefully evict you.

Speaker 1 (39:03):
Yeah, the sheriff told him that if you go into the
property like there's a biggreen no trespassing sign, if
you go into the property withoutpermission you can get arrested
.

Speaker 2 (39:14):
And so he asked me for permission and I just I
ignored it and I said no well,because it's a little bit of a
risk, right, like they weresupposed to leave december,
november 30th, right, andthey've been there that entire
time, so you let them back in.
It's like, well, okay, now yougot to call the sheriff back.
You're not going to physicallyforcefully remove somebody from
a building, right, so you juststart that process all over

(39:36):
again.
Potentially, that's the risk.

Speaker 1 (39:38):
Oh, potentially yeah.
Or he could have came into hisunit, he could have grabbed
something and, like you know,maybe that was a weapon, that
was the other thing that youwere aware that these tenants
did own firearms, and so it wasa real concern, real concern for
sure about just the process iswild.

Speaker 2 (39:55):
It's like you go through all of these steps and
hurdles just to get to the pointof getting control over the
property that you own again,just for them to like leave you
there with this person that youjust that you just made homeless
Right and not you, becauseobviously it was their actions
that led them to that point.
But that was a weird, likeemotional day, I feel like,

(40:16):
because we've been so frustratedabout this entire process and
how crazy it is, like I said,that you could own a property,
not be getting payment for itand literally have no control
over getting that property back.
But then we got to eviction dayand it was emotionally
upsetting because you realizenot that you didn't realize it,
but the reality of doing thisprocess is the result of

(40:39):
somebody standing outside thedoor saying I have nowhere to go
.
I have nowhere to go and thatdoesn't feel good.

Speaker 1 (40:48):
Oh no, that's the dirtiness of being a property
owner and providing housing topeople and unfortunately you
have to make these really hardcalls of.
I could have kept those guysthere, right, I could have
continued to allow them to stayin that unit.
They paid me their $950 rent.

(41:09):
The building just remainsdisgusting, impacting other
tenants, impacting other Becauseof this massive bug problem
that we have.
It's spilling over into otherparts of the building and it's
just, it's not sanitary and Ican't I, you know, I can't good
consciously say that I'mallowing these human beings to
live in a place that iscompletely unsanitary yeah, it

(41:31):
probably isn't even up to codewith those sanitation standards.
Oh, absolutely not, absolutelynot, absolutely not.
And so that that was kind ofwhat helped me, kind of like
personally get through all thisand realizing when I was,
because it's one thing if oflike personally get through all
of this and realizing what I was, because it's one thing if,
like you're just a piece of shittenant that's just not paying
you, and like you're causing allthis problem.
Yeah, kind of gaming the systemTotally gaming the system, and

(41:52):
that actually happened on.
We had another one of thosewhere actually, we did place
somebody.
This was somebody that we didplace and we got totally worked.
This was a professional tenantand this woman applied on the
unit but she met the criteriafor the unit in terms of income
and then her credit score.
And then all of a sudden shemoves in, she pays the first

(42:13):
couple of months of rent andI've got now I've got this guy
who was not on the lease, whodidn't follow through with the
application.
Now he's the guy I'm talking toin terms of when the rent's
being paid and who's paying it.
And now, all of a sudden, I gotthis phantom guy that I didn't
even know, that was living inthe unit, is now living in the

(42:33):
unit and I'm stuck because thenhe tells me hey, I'm not going
to pay you, and so now I'm in amoment of, as I'm going through
this other eviction process.
Well, I could start this, andwhich I certainly did, but then
I went to him and I said hey,man, we got to make, we got to
make a deal, and we made a deal,and I paid him $2,000 and they

(42:54):
vacated the unit and it was onlyjust a couple months of missed
rent two or three months ofmissed rent versus 10 months and
then we were able to getsomebody back in and a good
tenant that's now paying, and solong story short is that doing
a cash for keys deal like thatis absolutely what you want to

(43:16):
do.
You never, ever, want to takethis the distance, these
eviction things unless you haveunless you have to, unless
you're kind of forced to, inwhich we can.
We were forced to because thesewere incapacitated people and
they couldn't move out.

Speaker 2 (43:31):
And they told you to do the eviction notice so they
could try to get resources ontheir end as well.
Yeah, but yeah, either way,either scenario is it feels very
risky and like through theactual, like encounter that
occurs.

Speaker 1 (43:47):
Yeah.

Speaker 2 (43:48):
And it's, it's, it's weird emotion, cause you've got
the business side of it and thenyou've got the human side of it
and there's not.
There's not a perfect, easyanswer, but at the end of the
day, you can't live for free.

Speaker 1 (43:59):
Yeah, you can't.
You can't live for free.

Speaker 2 (44:00):
That's for sure.

Speaker 1 (44:01):
This is what it cost me.
It cost me about $1,600 so farfor legal fees, and then we
missed at least nine months ofrent.
Yeah, because it was December,and then it was September 15th
when they got out, so it was atleast nine and a half months.

Speaker 2 (44:16):
And they personally are out, but all their stuff is
still there.
So you still are not able to.

Speaker 1 (44:28):
So the eviction is done, but you are still not able
to access the unit yet becausetheir stuff has to be.
Yeah, it's going to be a full10 months of rent, yeah, yeah,
so it's going to be a full 10months of rent.
So that's going to be anothernine hundred ninety five hundred
dollars, yeah, so plus thesixteen hundred, so we're over
ten thousand in loss yeah, sofar.

Speaker 2 (44:38):
And if they choose not to take everything out
during their window, if they'relike, oh, I, oh, I'm just going
to grab a couple of personalitems and leave all of their
hoarding stuff then you've gotthat cost to incur.

Speaker 1 (44:48):
There's a turnover cost and renovation cost,
obviously, as we're going to gothrough all this.
So it's racking up, it's goingto get really expensive here,
but you know, this is all partof it and this is all part of
the risk as we start to realize,like boy, this would really
suck if this was the singlefamily home that we rented.
When you only have one tenantand that person decides to not
pay you anymore, all of a suddenyou are at a massive, massive

(45:11):
disadvantage.
It's insanely risky and we werejust lucky that we had four
other tenants in this onebuilding that were helping
support the mortgage and thatwas still.
That was fine, because that wassupporting the mortgage and we
were making those payments.
We weren't making any money onit, but like or we were making a
little bit of money on it, butlike we weren't really if we had
repairs and stuff.

(45:31):
Like all of a sudden it's tight, like we need that unit to get
up to the market value that webelieve it is to get us, you
know, in a lot better shape.

Speaker 2 (45:41):
Yeah, it makes those single unit rentals a lot less
attractive and something we'vebeen talking about quite a bit,
but we'll also say like this iswhere location really matters,
because we're talking aboutproperties in Cook County and in
Chicago and the tenant rightsthere are significantly more
favorable than they are in otherareas of the country.
So it'll, you know, depends onwhere you're at, where you own

(46:02):
property, right.

Speaker 1 (46:03):
Yeah, because you can just go over to Indiana and
they have a totally differentsystem where I believe it's like
you can have an eviction donein 60 days or something like
that, you know.
And or same thing in Tennessee.
I believe it's the and thoseare red, red States.
So it's kind of the differencebetween red and blue States here
.
But at the end of the day, Istill think Chicago is a great
place to invest.

(46:23):
It's just that you have tounderstand these issues and yeah
, but that's our story, that'sour story.
First eviction.
Hopefully you found some valuein that, and so now you can kind
of know what to expect.
At the end of the day.
I would not recommend aneviction.
I wouldn't recommend theattorney that I worked with.

Speaker 2 (46:39):
Didn't say his name, that's all right, no need

(47:06):
no-transcript.
Advertise With Us

Popular Podcasts

Stuff You Should Know
Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

CrimeLess: Hillbilly Heist

CrimeLess: Hillbilly Heist

It’s 1996 in rural North Carolina, and an oddball crew makes history when they pull off America’s third largest cash heist. But it’s all downhill from there. Join host Johnny Knoxville as he unspools a wild and woolly tale about a group of regular ‘ol folks who risked it all for a chance at a better life. CrimeLess: Hillbilly Heist answers the question: what would you do with 17.3 million dollars? The answer includes diamond rings, mansions, velvet Elvis paintings, plus a run for the border, murder-for-hire-plots, and FBI busts.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.