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  • 375. Why S Corporations Are a Disaster for Rental Properties (And How to Get Out)

    375. Why S Corporations Are a Disaster for Rental Properties (And How to Get Out)
    2026/04/28
    If you’ve ever been told to put your rental properties in an S corporation…this episode could save you thousands (or more) in taxes. In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nate Sosa break down one of the most common and expensive mistakes real estate investors make: holding rental properties inside an S corp. They cover: - Why S corporations don’t work for rental real estate - The hidden tax traps that can cost you big later - What happens when your property appreciates (and you want out) - Whether there’s any way to exit an S corp tax-free (spoiler: not really) - When S Corps actually do make sense in real estate Plus, they answer a common listener question: How many rental properties do you really need to qualify for Real Estate Professional Status? To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Get the FREE Ultimate STR Tax Strategy Bundle: go.therealestatecpa.com/strbundle 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.
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    30 分
  • MLRE: K-1s, Deadlines, and Tax Extensions: How Tax Season Is Hurting Your Long Game

    MLRE: K-1s, Deadlines, and Tax Extensions: How Tax Season Is Hurting Your Long Game
    2026/04/23
    In this episode, we’re breaking down one of the biggest misconceptions in real estate investing: the idea that you need to rush to file your taxes by April 15. If you’ve ever felt pressure to get your K-1s out early, file on time, or keep investors happy by hitting arbitrary deadlines, this episode is for you. We discuss why tax extensions are not only normal in the world of real estate syndications and funds, but often the smarter move. Rushing the process can lead to costly mistakes, amended returns, and unnecessary headaches for both operators and investors. You’ll learn how to properly set expectations with your LPs, why accuracy matters more than speed, and what really happens when you file without complete information. We also cover key lessons from this tax season, including common misunderstandings around bonus depreciation, passive losses, and how income from things like high-yield accounts can create unexpected tax implications. Plus, we walk through what you should be doing right now, post tax season, to review your returns, improve your processes, and plan ahead for the rest of the year. Request a free discovery meeting: go.therealestatecpa.com/mlre Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber 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.
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    22 分
  • 374. How People Make $50K Tax-Free Renting Their Home (Augusta Rule)

    374. How People Make $50K Tax-Free Renting Their Home (Augusta Rule)
    2026/04/21
    In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa break down the Augusta Rule, one of the most talked-about and misunderstood tax strategies in real estate. In this episode, we cover: - Where the Augusta Rule came from and how it ended up in the tax code - Who actually qualifies (and who doesn’t) - Why this strategy is often overhyped, especially for business owners - Real examples of homeowners earning $10K–$50K tax-free during major events - How events like the World Cup, Super Bowl, and Olympics can create big opportunities - The most common mistakes that can disqualify the strategy We also answer a listener's question about getting a rental property out of an S-corp and why that can become a tricky (and expensive) situation if you’re not careful. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Get the FREE Ultimate STR Tax Strategy Bundle: go.therealestatecpa.com/strbundle 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.
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    31 分
  • MLRE: Carried Interest: What’s Really Behind the “Loophole” and Why It's Misunderstood

    MLRE: Carried Interest: What’s Really Behind the “Loophole” and Why It's Misunderstood
    2026/04/16
    In this solo episode, Nate Sosa breaks down one of the most important — and most misunderstood — concepts in real estate syndication: carried interest. From its surprising origins in 16th-century shipping voyages to its modern-day use in private equity and real estate deals, Nate walks through how carried interest actually works, why it exists, and how it’s taxed. You’ll learn: - How GP/LP structures and waterfall distributions work - The difference between promote, profits interests, and equity - Why carried interest is taxed at favorable rates - The real risks GPs take (and why the upside exists) - What Congress has tried (and failed) to change about it - Common structuring mistakes that could trigger IRS issues Whether you’re an active sponsor or passive investor, this episode will help you better understand deal economics and what to watch for when evaluating opportunities. Request a free discovery meeting: go.therealestatecpa.com/mlre Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber 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.
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    19 分
  • 373. Insurance Mistakes Real Estate Investors Are Making (And What They’re Costing You)

    373. Insurance Mistakes Real Estate Investors Are Making (And What They’re Costing You)
    2026/04/14
    Most real estate investors spend a lot of time learning how to build wealth, but far fewer know how to protect it when disaster comes. In this episode, Thomas and Nate sit down with Michael Fried, Vice President and Partner at Strategic Claim Consultants, to break down what real estate investors need to know about insurance claims, asset protection, and avoiding costly coverage mistakes. Michael shares why insurance claims are so often underpaid, when investors should bring in a public adjuster, and how poor policy design can leave owners exposed after fires, water damage, storms, and other major losses. Whether you own one rental or a large portfolio, this episode will help you think more strategically about protecting your properties. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Get the FREE Ultimate STR Tax Strategy Bundle: go.therealestatecpa.com/strbundle 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.
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    38 分
  • MLRE: Why Multifamily Is Still Uninvestable (And Where Smart Money Is Going Instead) With Brian Burke

    MLRE: Why Multifamily Is Still Uninvestable (And Where Smart Money Is Going Instead) With Brian Burke
    2026/04/09
    Brian Burke, CEO of Praxis Capital and author of The Hands-Off Investor, joins the show to break down the current state of real estate investing and why he believes multifamily is still too early to touch. We discuss: - Why the multifamily market looks like a “traffic collision” right now - The biggest mistake investors make trying to time the bottom - Why senior housing may be the most overlooked opportunity today - The real impact of AI on real estate (and jobs) - Why tax benefits should NEVER be your primary investment thesis If you’re an LP or GP trying to navigate today’s uncertain market, this episode will help you think more strategically about timing, risk, and where the real opportunities are emerging next. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Aircraft Acquisitions White Paper: www.therealestatecpa.com/aircraft-white-paper/ 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.
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    38 分
  • 372. How Top Investors Handle Tax Deadlines (Strategic Extensions Explained)

    372. How Top Investors Handle Tax Deadlines (Strategic Extensions Explained)
    2026/04/08
    Tax extensions aren’t something to avoid. They’re something to understand and use strategically. In this episode, Nate Sosa and guest co-host Justin Shore break down why filing an extension is a normal (and often smart) move, even for tax professionals. They explain how extensions give you more time to file accurately, reduce costly mistakes, and help you stay in control of your tax strategy. You’ll also learn how to properly handle payments, avoid common penalties, and use extensions alongside quarterly estimates to stay compliant and efficient. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Get the FREE Ultimate STR Tax Strategy Bundle: go.therealestatecpa.com/strbundle 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.
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    26 分
  • MLRE: Disguised Sales: How Refinances Can Trigger Unexpected Taxes in Syndications

    MLRE: Disguised Sales: How Refinances Can Trigger Unexpected Taxes in Syndications
    2026/04/03
    In this episode of the Major League Real Estate Podcast, Thomas Castelli and Nate Sosa break down one of the most misunderstood areas of partnership tax law: disguised sales. While many investors assume distributions and refinance proceeds are tax-free, the rules change when partnerships and contributed property are involved. Get it wrong, and what you thought was a tax-free event could actually be treated as a taxable sale. You’ll learn: - How partnership distributions actually work (and how they affect your basis) - What a disguised sale is and why the IRS cares - The 2-year rule that can trigger unexpected taxes If you’re a syndicator, GP, or investor contributing property into deals, this episode is a must-listen to avoid costly tax mistakes. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Aircraft Acquisitions White Paper: www.therealestatecpa.com/aircraft-white-paper/ 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.
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    21 分