Tax Smart Real Estate Investors Podcast

Tax Smart Real Estate Investors Podcast

The Tax Smart Real Estate Investors Podcast is a show that focuses on tax, accounting, and finance tips for real estate investors and business owners. We bring on guests to talk through complex topics and we break it down into bite-sized chunks of knowledge for our listeners. Our episodes generally run 30-60 minutes of no-nonsense, hard-hitting information. We know your time is valuable so our goal is to save you thousands of dollars per episode. Hall CPA, PLLC is a CPA firm that exclusively serves real estate investors and real estate business owners. We work with syndicators and developers closing multi-million dollar deals, as well as small investors building a portfolio from scratch. Check us out at www.TheRealEstateCPA.com/Podcast for more free content and information. Enjoy! The Tax Smart Real Estate Investors podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor

Episodes

400. The Core Tax Strategy Blueprint: The Plan We Give our Top Clients

October 20, 2026 • 40 mins
In this episode of the Tax Smart REI podcast, Tom and Nate break down the core tax strategy playbook used by real estate investors and high-income earners to minimize their tax burden before year-end. They dive deep into the real estate professional status (REPS) requirements, the short-term rental loophole, grouping elections, cost segregation, and 100% bonus depreciation. They also evaluate exit strategies like 1031 exchanges, ...
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Investing by Gut Feeling? Why Data Beats It “by a Million Miles” with Neal Bawa

October 15, 2026 • 49 mins
Neal Bawa, a former tech founder who has invested in apartments since 2013, joins Nate and Tom to talk about using data to make real estate decisions. He explains why he passed on investing in Huntsville, Alabama, despite its growth, and where he sees multifamily rents heading over the next two years. He also discusses how Claude now handles much of his underwriting, from screening incoming deals to pulling comps and building das...
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399. Thinking About a 1031 Exchange? 5 Key Questions to Consider with Julia Fritzlen

October 13, 2026 • 36 mins
In this episode of the Tax Smart REI podcast, Tom and Nate welcome Julia Fritzlen of Insight Investment Advisors to talk about helping real estate owners exit without a large tax bill. Julia explains how she moved from healthcare equipment financing into 1031 exchanges and Delaware Statutory Trusts (DSTs), and why she starts every conversation by asking what life should look like after the property is gone. The group covers the...
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Claim Denied: The Insurance Mistakes That Could Cost You

October 8, 2026 • 27 mins
Nobody wants to talk about insurance until something goes wrong. In this episode of the Major League Real Estate Podcast, Nate and Tom walk through real court cases and news stories showing how real estate investors lose coverage over technicalities, from misstating a property's use (single-family vs. short-term rental) to deeding it to an LLC or family trust without updating the policy. They also cover outdated replacement-cost e...
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398. 4 Ways Your Short-Term Rental Occupancy Tax Can Go Wrong with Serena Verma

October 6, 2026 • 31 mins
Airbnb may be collecting occupancy tax for you, but that doesn't mean you're in the clear. In this episode of the Tax Smart REI podcast, Tom and Nate talk with Serena Verma, founder of Hostvisors and Monterra Tax, about an audit that uncovered $250,000 in tax exposure and the four ways occupancy tax goes wrong: over-collection, under-collection, over-remittance, and under-remittance. She also explains why platforms like Airbnb, VR...
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Investing in the “Infrastructure of Daily Life”: Express Car Washes, Oil Changes, Healthcare, & More with Chris Salerno

October 1, 2026 • 45 mins
What happens when a real estate investor decides traditional multifamily no longer offers the opportunities it once did? In this episode of the Major League Real Estate Podcast, Nate and Tom sit down with Chris Salerno, founder and CEO of QC Capital Group, to discuss why he moved beyond multifamily into express car washes, oil changes, flex industrial real estate, healthcare, and other alternative investments. Chris shares how he...
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397. How a Pharmacist Built a 14-Property Student Housing Portfolio with Ryan Chaw

September 29, 2026 • 35 mins
Ryan Chaw went from working long shifts as a pharmacist to owning 14 student rentals with 90 tenants. He joins Tom and Nate to explain how he built his portfolio using a rent-by-the-room strategy while still working his W-2 job. Ryan talks about the expensive mistakes he made on his first property, what he looks for when buying student rentals, and how he manages his portfolio. He also shares how rental income allowed him to leave...
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Why This $100M+ Investor Traded Apartments for Manufactured Homes With John Cohen

September 24, 2026 • 38 mins
John Cohen, co-founder of Toro Real Estate Partners and JC Property Group, joins Nate and Tom to break down a real estate journey that started with $300 tax deed auctions and grew into hundreds of millions in multifamily, land, and development deals. John explains why he and his team sold almost their entire multifamily portfolio between 2020 and 2023 right before interest rates spiked, why he believes multifamily is a great long...
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396. 60 Days Left To Buy A Short-Term Rental For 2026 Tax Savings

September 22, 2026 • 34 mins
With Q4 underway, time is running out to put the short-term rental tax strategy to work for 2026. In this episode of the Tax Smart REI Podcast, Tom and Nate sit down with returning guest Justin Shore to break down the real "60-day countdown" investors face if they want to close on a property, get it rented, and qualify for STR tax benefits before year-end. They cover how many guest stays you actually need, why personal use in yea...
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Your Real Estate Is Insured. But Are You Actually Covered?

September 17, 2026 • 18 mins
Having insurance doesn’t necessarily mean your real estate investment is fully protected. In this episode of the Major League Real Estate Podcast, Tom and Nate discuss why market value, loan balance, insurance limits, and replacement costs can all be different, and why simply meeting your lender’s insurance requirements may leave your equity exposed. They also explain what happens when insurance proceeds exceed the c...
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395. Debunking 5 Material Participation Myths Real Estate Investors Keep Getting Wrong

September 15, 2026 • 28 mins
Material participation is one of the most important and misunderstood tax rules for real estate investors. In this episode of the Tax Smart REI Podcast, Tom and Nate debunk five common myths involving Real Estate Professional Status (REPS), short-term rentals, the 100-hour test, property managers, equipment rentals, and partnerships. They also explain when a spouse’s hours count toward material participation, why those ho...
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Why Mobile Home Parks Might Be the Best Tax Play in 2026 with Michael Pansolini

September 10, 2026 • 34 mins
Michael Pansolini went from PwC and Brookfield to buying mom-and-pop mobile home parks. In this episode, he breaks down why he believes the asset class presents such a compelling opportunity for real estate investors. Michael joins Nate and Tom to explain how his experience underwriting institutional real estate helped him build his own mobile home park portfolio and eventually co-found MHP Pros. They dive into what makes mobile ...
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394. 10 Years of Hall CPA: From Startup to a $17M Real Estate CPA Firm with Brandon Hall

September 8, 2026 • 39 mins
Hall CPA is officially 10 years old, and Founder & CEO, Brandon Hall is back on the Tax Smart REI Podcast to talk about how the firm got to where it is today. In this special anniversary episode, Brandon joins Tom and Nate to look back at Hall CPA’s journey from answering real estate tax questions online to building a $17 million real estate CPA firm and becoming a Top 400 CPA firm in the United States. Brandon shares t...
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The 1031 Exchange Holding Period Myth with Matthew Rappaport (Part 2)

September 3, 2026 • 32 mins
In Part 2 with tax attorney Matthew Rappaport, we go deeper into the complexities of 1031 exchanges for real estate partnerships. Matt breaks down the holding-period myth behind drop-and-swaps, why transaction sequencing matters, and how the risks can differ in California and New York. We also explore partnership divisions under Section 708, why special allocations often don’t work, the limitations of Section 761(a) election...
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393. The Truth About Buying a Short-Term Rental for Tax Benefits: Joey Linn’s First Deal, a Flood & What He Learned

September 1, 2026 • 35 mins
Joey Linn went from covering NBA stars for Sports Illustrated to buying and remotely managing his first short-term rental in Michigan City, Indiana. The original motivation? A growing business had created a significant tax problem, and Joey saw short-term rental real estate as an opportunity to combine potential tax benefits with an appreciating, cash-flowing asset. But his first deal quickly became a real-world education in real...
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What Investors Get Wrong About 1031 Exchanges & Drop and Swaps with Matthew Rappaport (Part 1)

August 27, 2026 • 28 mins
This week on the Major League Real Estate Podcast, we're kicking off a two-part conversation with tax attorney Matthew Rappaport, Chair of the Taxation and Private Client Groups and Vice Managing Partner at Falcon Rappaport & Berkman. In Part 1, Nate and Matthew break down what happens when real estate partners want to sell the same property but have different plans for the proceeds. Matthew then goes into partnership 1031 ex...
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392. Could Trump Index Capital Gains for Inflation and Lower Your Tax Bill?

August 25, 2026 • 29 mins
Could capital gains taxes eventually be adjusted for inflation, and could the home sale exclusion increase from $500,000 to $1 million for married couples filing jointly? In this episode of the Tax Smart REI Podcast, Nate Sosa and Justin Shore break down the discussion around capital gains indexing, how an inflation adjustment to tax basis could work, and why changes to the Section 121 home sale exclusion could have a significant ...
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Advanced Estate & Trust Tax Strategies for Real Estate Investors (And Why They Matter)

August 20, 2026 • 25 mins
In this MLRE episode, Nate and Tom continue their estate and trust planning series by exploring more advanced strategies investors should understand. They break down grantor vs. non-grantor trusts, intentionally defective grantor trusts, the trade-off between estate tax savings and the step-up in basis, and how strategies such as SLATs, GRATs, QPRTs, and dynasty trusts can fit into an estate plan. They also explain why estate plan...
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391. Can This “Disaster Relief” Tax Strategy Really Offset W-2 Income?

August 18, 2026 • 25 mins
In this episode, Tom and Nate break down a disaster relief housing promotion involving metal container housing, special grantor trusts, material participation, and significant first-year depreciation deductions. They also examine additional red flags surrounding the financing, at-risk rules, potential cancellation of debt, depreciation recapture, and what taxpayers should do when they're presented with an aggressive strategy that ...
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5 Real Estate Syndication Tax Questions Every LP Should Know

August 13, 2026 • 24 mins
In this episode of the Major League Real Estate Podcast, Nate Sosa and Thomas Castelli break down some of the most common tax questions real estate sponsors hear from limited partners. When should LPs expect their K-1s? Can passive real estate losses offset W-2 income? Do you need an LLC to invest in a syndication? What happens when you invest through a retirement account? And what happens from a tax perspective when the property ...
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