In this episode of the Tax Smart REI Podcast, Thomas, Troy, and Ryan unpack real IRS audit case studies involving real estate investors and break down exactly what happened, how they responded, and how they won.

Tune in to learn:

- What triggers IRS audits for short-term rentals and REPS (and how to avoid them)

- The one thing most CPAs get wrong when representing clients in an audit

- How a $209K tax bill was reduced to $296—with documentation and strategy

- Why being “audit-ready” matters more than ever in the post-TCJA world

- What to do (and not do) the moment you receive that dreaded IRS letter

If you want to understand what an audit really looks like and how to protect yourself before one ever happens, this episode is a must-listen.

To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6

Subscribe to REI Daily & Enter to Win a FREE Strategy Call:

go.therealestatecpa.com/41JuQBX

Join the Tax Smart Insiders Community:

go.therealestatecpa.com/3Xx1Cpd

Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli

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.

In this week’s episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa break down what real estate investors need to know about the draft of the 2025 tax bill, dubbed the “One Big, Beautiful Bill”, including what’s in it, what might change, and how to prepare for the opportunities it presents.

Key topics covered:

- The likely return of 100% bonus depreciation (and who qualifies)

- SALT cap drama: why it could derail the bill

- Changes to Qualified Opportunity Zones and what they mean for investors

- Section 179 expensing increases for short-term rentals and asset-heavy businesses

- QBI deduction bumps and simplified rules for service-based businesses

- Full expensing for industrial facilities (and how it could spark a manufacturing boom)

- “No tax on tips, overtime, or Social Security” — what made it in and what didn’t

Plus, we cover what provisions are being made permanent, what’s being rolled back, and why now is the time to align with a tax advisor who knows how to play offense with the tax code.

To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6

Subscribe to REI Daily & Enter to Win a FREE Strategy Call:

go.therealestatecpa.com/41JuQBX

Join the Tax Smart Insiders Community:

go.therealestatecpa.com/3Xx1Cpd

Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli

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.

In this week’s episode of the Tax Smart REI Podcast, Thomas Castelli and Ryan Carriere break down what real estate investors need to know about the upcoming 2025 tax bill, including where it stands, what’s likely to be included, and how it could impact your bottom line.

Key topics covered:

- Expected return of 100% bonus depreciation

- Potential changes to the SALT deduction cap

- How to properly log hours for REPS (Real Estate Professional Status)

- Using the STR loophole for boutique hotels

- Depreciating furniture in furnished rentals

- Grouping LP losses with active rentals

- Why tax planning still matters, even if you don’t qualify for REPS or STR

Plus, we tackle common mistakes CPAs make and discuss whether setting up a property management company for your own rentals actually makes sense.

To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6

Subscribe to REI Daily & Enter to Win a FREE Strategy Call:

go.therealestatecpa.com/41JuQBX

Join the Tax Smart Insiders Community:

go.therealestatecpa.com/3Xx1Cpd

Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli

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.

In this post 4/15 recap, Thomas and Ryan reflect on the key themes and expert interviews from the year so far, from tiny homes to creative finance, and reinforce a common truth: smart investing still works in today’s market if you stay focused and play the long game.

They also dive into what’s happening with the 2025 tax bill, including the outlook on 100% bonus depreciation, and answer real investor questions from email and the Tax Smart Facebook group.

Topics include:

- Real estate investment takeaways from interviews with Robuilt, Avery Carl, Henry Washington, and more

- What to do (and not do) after 4/15 for tax savings

- The latest on the 2025 tax bill and bonus depreciation

- How step-up in basis affects depreciation

- Using Form 3115 to catch up on missed depreciation

- REPS Log and time tracking for short-term rental investors

- Why LP losses don’t offset W-2 income—and what to do about it

- The lazy 1031 exchange strategy for exiting syndications

Remember to submit your questions at [email protected] or the Tax Smart Investors Facebook group.

To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6

Subscribe to REI Daily & Enter to Win a FREE Strategy Call:

go.therealestatecpa.com/41JuQBX

Join the Tax Smart Insiders Community:

go.therealestatecpa.com/3Xx1Cpd

Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli

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.

In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with multifamily syndication expert Michael Blank to unpack why 2025 may be one of the best times in years to get started—or scale—in multifamily real estate.

Tune in to learn:

- Why today’s market conditions offer lower risk and higher long-term upside.

- How Michael bounced back from losing millions to build a $300M multifamily portfolio.

- What’s really driving investor hesitation—and how to overcome it.

- How tariffs, inflation, and interest rates are reshaping deal underwriting.

- Why syndication outpaces the BRRRR strategy for wealth and time freedom.

If you’ve been thinking about making the leap from single-family to multifamily—or are just curious what’s working in today’s unpredictable environment—this episode is packed with insights from one of the top minds in the business.

To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6

Subscribe to REI Daily & Enter to Win a FREE Strategy Call:

go.therealestatecpa.com/41JuQBX

Join the Tax Smart Insiders Community:

go.therealestatecpa.com/3Xx1Cpd

Training from Michael:

thefreedompodcast.com/thomas

Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli

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.

In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with seasoned real estate investor and author Henry Washington to discuss why he’s not chasing creative finance trends, and why his “boring” strategy continues to deliver results in 2025’s unpredictable market.

Tune in to learn:

- Why Henry sticks with off-market deals and direct mail (even in the age of AI).

- How he adjusts his strategy based on market cycles—without overreacting to headlines.

- Why he believes helping sellers matters more than squeezing every dollar.

- How to find pain points in the market—and actually solve them.

- What newer investors get wrong by chasing the “next big thing.”

If you’re looking for a grounded, proven approach to real estate investing, even in times of rising rates and economic uncertainty, this episode will give you clarity and confidence.

To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6

Subscribe to REI Daily & Enter to Win a FREE Strategy Call:

go.therealestatecpa.com/41JuQBX

Join the Tax Smart Insiders Community:

go.therealestatecpa.com/3Xx1Cpd

Connect with Henry on Instagram: @thehenrywashington

Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli

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.

In this episode of the Tax Smart REI Podcast, Thomas and Ryan talk with wealth manager Connor Low, founder of Iarann Wealth, about how today’s economic uncertainty, from global tariffs to interest rate swings, is impacting investors, and what real estate investors should be doing about it.

Connor breaks down the current market landscape, explains why panic is rarely a productive move, and shares how both real estate and equity investors can make smart, intentional decisions during periods of volatility.

Tune in to learn:

- Why today’s stock market volatility is driven more by emotion than economic data.

- How real estate investors can take advantage of discounted equities without abandoning their REI strategy.

- The right (and wrong) times to rebalance, lump-sum invest, or just sit tight.

- Why Connor isn’t bullish on infinite banking—and what he recommends instead.

- How his goal-based planning model helps investors make smarter decisions with both real estate and the stock market.

To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6

Subscribe to REI Daily & Enter to Win a FREE Strategy Call:

go.therealestatecpa.com/41JuQBX

Join the Tax Smart Insiders Community:

go.therealestatecpa.com/3Xx1Cpd

Connect with Conner: iarannwealth.com

Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli

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.

In this episode, Thomas and Ryan share real-life case studies from real estate investors who used strategic tax planning to save thousands, sometimes hundreds of thousands, on their tax bills. They also reveal the most common mistakes and missed opportunities they see from investors who waited too long or relied on the wrong advice.

This episode explores:

- How one couple saved $285K in a single year using REPS and cost segregation.

- Why timing matters when using the short-term rental loophole—and how to get it right.

- What happens when a CPA mistakenly opts you out of bonus depreciation.

- How a non-REPS investor reduced their taxes by $40K annually—without changing jobs.

- Real examples of costly filing mistakes, disqualified STRs, and even unintentional fraud.

If you're serious about using real estate to build wealth and reduce taxes, while avoiding irreversible errors, this is an episode you can’t afford to skip.

To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6

Subscribe to REI Daily & Enter to Win a FREE Strategy Call:

go.therealestatecpa.com/41JuQBX

Join the Tax Smart Insiders Community:

go.therealestatecpa.com/3Xx1Cpd

Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli

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.

In this Q&A episode, Ryan and Thomas answer real estate investors’ most pressing tax questions. From short-term rental loopholes to QBI deductions, they break down some of the most misunderstood topics in real estate tax strategy and provide practical, real-world guidance.

They discuss:

- STR Losses & NOLs

- Travel Time & Material Participation

- QBI Safe Harbor

- STR Conversions Mid-Year

- Bonus Depreciation Recapture

- Home Improvement Records

- The 14-Day Rule Explained

Remember to submit your questions at [email protected] or the Tax Smart Investors Facebook group.

To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6

Subscribe to REI Daily & Enter to Win a FREE Strategy Call:

go.therealestatecpa.com/41JuQBX

Join the Tax Smart Insiders Community:

go.therealestatecpa.com/3Xx1Cpd

Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli

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.

In this episode of the Tax Smart REI Podcast, Thomas Castelli and Ryan Carriere are joined by Chris Prefontaine, real estate veteran, founder of Smart Real Estate Coach, and leader of the Wicked Smart Community.

Chris brings over three decades of experience to the table and breaks down how to invest without banks, structure zero-interest seller financing deals, and navigate subject-to transactions with confidence. You'll also hear about:

- Why 2008 changed the way Chris does business forever

- How creative financing works in any market cycle

- The power of principal-only payments

- Real-world examples of building long-term wealth without traditional loans

Whether you're looking to grow your long-term rental portfolio, invest in short-term rentals, or just want to stop competing in the bank-financed rat race, this episode is packed with insights and strategy.

To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6

Subscribe to REI Daily & Enter to Win a FREE Strategy Call:

go.therealestatecpa.com/41JuQBX

Join the Tax Smart Insiders Community:

go.therealestatecpa.com/3Xx1Cpd

Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli

Free Resources from Chris:

Get his best-selling book FREE at wickedsmartbooks.com/TSI

Watch his free creative financing workshop: smartrealestatecoach.com/mastersclass

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.