Tax Smart Real Estate Investors Podcast

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...

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 expl...

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...

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...

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 bel...

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 actua...

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 p...

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 pa...

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....

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 S...

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 limitation...

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 beca...

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...

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 e...

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....

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...

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...

Some tax decisions are easy to change. Others can lock you into a strategy you may not be able to undo. In this episode of the Tax Smart REI Podcast, Nate Sosa sits down with Hall CPA Senior Advisory Manager Justin Shore to break down tax elections that real estate investors need to understand before filing their returns. They discuss how elections can be buried inside a tax return or even be made...

Why aren't we putting more emphasis on estate planning? In this episode, Nate Sosa and Thomas Castelli break down the essential estate planning strategies every real estate investor should understand. They cover why a simple will often isn't enough, how living trusts help avoid probate, the importance of powers of attorney and healthcare directives, and how estate planning intersects with tax plan...

Many real estate investors assume that holding land for several years automatically qualifies them for favorable capital gains treatment. Unfortunately, that's not always true. In this episode, we break down one of the most misunderstood areas of real estate taxation: dealer status. You'll learn how the IRS determines whether your land is an investment or inventory, why intent alone isn't enough,...

Many real estate investors assume that as their business grows, qualifying for Real Estate Professional Status becomes automatic. The reality is much more complicated. In this episode, Nate and Tom tackle the question: Can you become too big for REPS? They break down what actually qualifies as material participation, whether capital raising counts toward REPS, how delegation changes the analysis,...

Trump Accounts are now live, giving parents and grandparents another option for saving and investing on behalf of their children. In this episode of the Tax Smart REI Podcast, Thomas Castelli, Jacob Orr, and Nate Sosa discuss how Trump Accounts work, who qualifies, how the government's $1,000 contribution is claimed, and where these accounts fit alongside strategies like 529 plans, Roth IRAs, and...

Commercial real estate is changing, and the smartest investors are already adapting. In this episode, Nate Sosa and Thomas Castelli sit down with Mark Sinnett, Head of Capital Markets for Quebec at Avison Young. After closing more than 800 commercial real estate transactions totaling over $10 billion, Mark shares what institutional investors are seeing before everyone else. They discuss: - Why ret...

How does someone go from working in their family's Italian restaurant to building a $400 million multifamily real estate portfolio? In this episode, Gino Barbaro shares the lessons that transformed his life, from losing money in his first investment to building over 2,000 apartment units with his partner Jake Stenziano. We discuss: - Why today's multifamily market looks surprisingly similar to 201...

Update: The 21st Century ROAD to Housing Act became law on July 11, 2026, after President Trump neither signed nor vetoed the bill within the constitutional deadline. In this episode, Nathan sits down with Troy Silfies, VP of Tax at Hall CPA, to discuss the new 21st Century Housing Bill and what it could mean for investors, builders, landlords, lenders, and prospective homebuyers. Together, they e...