Short-Term Rentals, Real Talk: Lessons from 6 Years Hosting & What Smart Investors Are Doing Next

I’m pulling back the curtain on how we got started in real estate investing.  Spoiler alert: it all began with an Airbnb in our backyard. In this minisode, I’m sharing the behind-the-scenes of our six-year journey with short-term rentals—from building our ADU to navigating Portland’s ever-evolving STR laws, managing (and outsourcing) guests, and yes... restocking way too much toilet paper.

If you’re thinking about turning your space into a short-term rental or just curious about how STRs actually work, this episode is packed with honest insights, lessons learned, and practical tips for new and seasoned hosts alike. I’m also diving into what I believe is the next wave for real estate investors—and why the Airbnb model may not be the golden ticket it once was.

Here are the top takeaways from this episode:

1. Start with the Worst-Case Scenario to Run the Numbers

Before falling in love with Airbnb income projections, ground yourself in financial reality. Ann recommends always asking: Would this property still make sense as a long-term rental?

2. Know the Rules Before You Buy (and Expect Them to Change)

Short-term rental success isn’t just about aesthetics and occupancy—it's about legality. Understanding permitting, zoning, taxes, and even HOA restrictions can make or break your investment.

3. STRs Are Seasonal, Hands-On, and Require Replenishable Inventory

Cash flow might be stronger than long-term rentals, but you’re essentially running a mini hotel. STRs require ongoing expenses, restocking, and attention to comfort and cleanliness.

4. Property Management Isn’t All or Nothing, Find a Hybrid Model

If you don’t want to be glued to your phone managing guest check-ins, consider hybrid options. Tech tools and part-time managers can help balance profitability and peace of mind.

5. Trends Change, Be Willing to Evolve

Market cycles matter. Ann reminds us to zoom out and consider new models like midterm rentals or co-living before jumping into saturated strategies.

Want to learn more about real estate investing? Hop on the waitlist for the Soulful Investor Society, a community membership for real estate investors and those who'd like to get in the game. Once on the waitlist, you'll be the first to know when the doors open AND you'll get lots of amazing freebies, including a FREE 1:1 coaching session with me, where we'll map out your plan from start to finish, so you can finally buy that investment property and scale your portfolio. 

You can also find me on IG @annreedandco where I share daily musings on real estate, mindfulness, being an almost empty nester, and more.