The most played episodes among Podcast App listeners.

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   Number 1: What Investors Get Wrong About 1031 Exchanges & Drop and Swaps with Matthew Rappaport (Part 1)

   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.

   August 27, 2026·29min
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   Number 2: Advanced Estate & Trust Tax Strategies for Real Estate Investors (And Why They Matter)

   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.

   August 20, 2026·26min
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   Number 3: 395. Debunking 5 Material Participation Myths Real Estate Investors Keep Getting Wrong

   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 hours cannot be combined to meet the 750-hour REPS requirement, and what investors should know about Deferred Sales Trusts (DSTs). If you’re using real estate losses as part of your tax strategy, this episode covers the material participation rules and misconceptions you need to understand. 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.

   September 15, 2026·29min
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   Number 4: Your Real Estate Is Insured. But Are You Actually Covered?

   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 cost of rebuilding, when those proceeds can create a taxable gain, and how Section 1033 may allow investors to defer that gain following certain involuntary conversions. Plus, they cover insurance reviews, replacement costs, entity details, documentation, and why investors and syndicators should regularly make sure their coverage matches their actual risk. Request a free discovery meeting: go.therealestatecpa.com/mlre 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.

   September 17, 2026·19min
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   Number 5: The 1031 Exchange Holding Period Myth with Matthew Rappaport (Part 2)

   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 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.

   September 03, 2026·33min
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