Tax Smart Real Estate Investors Podcast

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) elections, and what Rev. Proc. 2002-22 actually means for tenancy-in-common arrangements.

Request a free discovery meeting: go.therealestatecpa.com/mlre

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The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, 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.

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 estate investing.

In this episode, Joey joins Thomas Castelli, CPA, and Nate Sosa to explain why he invested in the Midwest instead of Southern California, how he bought his first property without seeing it in person, and how he built a local team to manage the property remotely.

Plus, Joey shares his journey from sports media to entrepreneurship, how AI is changing the sports-writing business, and what could be next for his real estate portfolio.

Request a consultation from Hall CPA at go.therealestatecpa.com/taxsmart

Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup

Join the Hall CPA Team: go.therealestatecpa.com/team

Submit your question for Tom & Nathan: go.therealestatecpa.com/question

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.

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 exchanges and the strategy commonly known as a "drop and swap," including why a reorganization may be necessary when one partner wants to exchange while another wants to cash out or when multiple partners want to pursue different replacement properties.

They also discuss some of the costly mistakes that can put these transactions at risk, from failing to coordinate tax counsel, accountants, qualified intermediaries, brokers, and lenders to overlooking critical formalities involving ownership, agreements, insurance, banking, and tax reporting.

Matthew also explains why New York and California deserve special attention, how state tax authorities scrutinize these transactions, and several of the court cases that have shaped today's 1031 landscape.

And this is only Part 1.

Request a free discovery meeting: go.therealestatecpa.com/mlre

Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup

Join the Hall CPA Team: go.therealestatecpa.com/team

Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide

Submit your questions to: go.therealestatecpa.com/question

The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, 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.

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 impact on homeowners and real estate investors.

Plus, Nate and Justin examine another major shift happening inside the accounting industry: private equity-backed consolidation, accounting firm roll-ups, and what those changes could mean for employees and clients.

Request a consultation from Hall CPA at go.therealestatecpa.com/taxsmart

Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup

Join the Hall CPA Team: go.therealestatecpa.com/team

Submit your question for Tom & Nathan: go.therealestatecpa.com/question

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.

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 planning shouldn’t be treated as a one-time exercise, and why getting the basics in place early matters even if your net worth is currently below the estate tax exemption.

Request a free discovery meeting: go.therealestatecpa.com/mlre

Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup

Join the Hall CPA Team: go.therealestatecpa.com/team

Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide

Submit your questions to: go.therealestatecpa.com/question

The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, 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.

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 sounds too good to be true.

Request a consultation from Hall CPA at https://go.therealestatecpa.com/taxsmart

Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup

Join the Hall CPA Team: https://go.therealestatecpa.com/team

Submit your question for Tom & Nathan: go.therealestatecpa.com/question

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.

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 finally sells?

Nate and Tom also unpack depreciation recapture, UBIT and UDFI, passive loss carryforwards, and why an individual LP generally can't simply initiate a 1031 exchange when a syndication sells.

Request a free discovery meeting: go.therealestatecpa.com/mlre

Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup

Join the Hall CPA Team: www.therealestatecpa.com/careers/

Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide

Submit your questions to: go.therealestatecpa.com/question

The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, 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.

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 simply by failing to file a form or check the right box. Nate and Justin cover real estate professional status and grouping elections, opting out of bonus depreciation, installment sales, 1031 exchanges, Section 754 elections, and grouping businesses under the passive activity rules.

They also explain why timing matters, when an election can restrict future tax-planning opportunities, and why investors should understand the decisions being made on their returns rather than simply signing and filing.

If you're buying or selling real estate, claiming depreciation, qualifying as a real estate professional, or making other major tax moves, this episode highlights the questions you should be asking your tax professional before the return is filed.

Request a consultation from Hall CPA at go.therealestatecpa.com/3KSEev6

Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup

Join the Hall CPA Team: www.therealestatecpa.com/careers/

Submit your question for Tom & Nathan: go.therealestatecpa.com/question

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.

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 planning.

They also discuss estate tax exemptions, the step-up in basis, gifting strategies, and when more advanced trusts may become necessary as your portfolio grows.

Request a free discovery meeting: go.therealestatecpa.com/mlre

Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup

Join the Hall CPA Team: www.therealestatecpa.com/careers/

Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide

Submit your questions to: go.therealestatecpa.com/question

The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, 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.

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, and how seemingly small decisions before a sale can dramatically impact your tax bill.

We discuss the seven factors courts use to evaluate dealer status, real-world tax court cases, why 1031 exchanges and installment sales may no longer apply if you're classified as a dealer, and how entity structuring may help strengthen your position.

Whether you're land banking, flipping properties, developing real estate, or simply planning your next investment, understanding these rules could save you hundreds of thousands of dollars in unnecessary taxes.

Request a consultation from Hall CPA at go.therealestatecpa.com/3KSEev6

Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup

Join the Hall CPA Team: www.therealestatecpa.com/careers/

Submit your question for Tom & Nathan: go.therealestatecpa.com/question

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.