In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa field real questions from the Tax Smart Investors Facebook group, their online community, and recent client conversations to tackle the most common and most confusing year-end tax issues real estate investors are facing.

You’ll learn:

- Why you must take depreciation on your rental properties

- When you’re stuck with 40% vs 100% bonus depreciation

- How short-term rental hours do (and don’t) count toward real estate professional status

- When using a property manager or a seller staying in the property after closing can blow up your short-term rental strategy

- The tests you need to meet if you want syndication losses to be non-passive

- Why condos still need a land allocation for depreciation even if you “don’t own the dirt”

Practical year-end action items: time logs, charitable bunching, retirement contributions, and how to use the free Year-End Tax Checklist without panic-buying a bad deal for a one-year tax win

Whether you’re trying to squeeze in a year-end short-term rental, line up a cost seg study, or simply avoid costly mistakes on your 2025 return, this episode will help you zoom out, think long term, and decide which moves are truly worth making before December 31st — and which ones can wait.

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

Connect with Engineered Tax Services:

https://portal.engineeredtaxservices.com/cost-segregation/quick-start?utm_source=Live+Event&utm_medium=Others&utm_campaign=hall_cpa&pagesense_source=729733000061045013&utm_term=kim_lochridge&utm_content=cost_segregation

Get the Year-End Tax Checklist:

https://go.therealestatecpa.com/4pj63id

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 Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa, Head of the National Tax Department at Hall CPA, sit down with Alex Savage, CPA, CFP, to unpack the Mega Backdoor Roth 401(k), one of the most powerful yet underutilized tax strategies for high-income earners.

They break down how the strategy works, who qualifies, and why it can be a game-changer for those looking to build long-term, tax-free retirement wealth, all while balancing real estate investing and other income streams. From contribution limits and in-plan conversions to control group rules and timing, this episode covers everything you need to know to decide whether this advanced strategy fits your situation.

You’ll learn:

- What makes the “Mega” Backdoor Roth 401(k) different from a traditional or standard Roth IRA

- How high-income W-2 earners and solopreneurs can contribute up to $70,000+ in after-tax dollars

- Why this strategy can help you manage future tax rates, Social Security taxation, and estate planning

- The key testing and timing rules to avoid IRS pitfalls

- When a Mega Backdoor Roth makes sense and when real estate might be the better play

Whether you’re a tech executive, business owner, or high-earning real estate investor, this episode gives you the clarity to determine if the Mega Backdoor Roth 401(k) belongs in your financial toolkit and how to use it strategically alongside your real estate portfolio.

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

Connect with Engineered Tax Services:

https://portal.engineeredtaxservices.com/cost-segregation/quick-start?utm_source=Live+Event&utm_medium=Others&utm_campaign=hall_cpa&pagesense_source=729733000061045013&utm_term=kim_lochridge&utm_content=cost_segregation

Get the Solar White Paper:

www.therealestatecpa.com/solar-white-paper/

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 Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa, Head of the National Tax Department at Hall CPA, dive deep into solar tax credits: how they work, who qualifies, and whether they can truly offset your tax liability as a real estate investor.

From residential installations to short-term rentals and syndicated solar investments, Thomas and Nathan unpack the real opportunities and limitations of this increasingly popular strategy. They break down how the 30% credit applies, what deadlines matter, and why material participation plays a critical role in determining whether your solar investment is active or passive for tax purposes.

You’ll learn:

- How the 30% solar tax credit works for personal, rental, and business properties

- The key deadlines for claiming residential solar credits before they expire in 2025

- Why material participation determines if your solar credits can offset active income

- How to combine bonus depreciation and solar credits for a “double benefit”

- The truth about syndicated solar credit deals and whether they’re legitimate

Whether you’re curious about installing solar on your own properties or exploring syndicated solar investments, this episode gives you a clear-eyed look at the tax benefits, the fine print, and the pitfalls to avoid before making your next move.

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

Connect with Engineered Tax Services:

https://portal.engineeredtaxservices.com/cost-segregation/quick-start?utm_source=Live+Event&utm_medium=Others&utm_campaign=hall_cpa&pagesense_source=729733000061045013&utm_term=kim_lochridge&utm_content=cost_segregation

Get the Solar White Paper:

https://www.therealestatecpa.com/solar-white-paper/

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 Tax Smart REI Podcast, Thomas Castelli and Justin Shore discuss essential year-end tax strategies for real estate investors looking to close out 2025 strong. As Q4 winds down, they walk through the most effective levers you can pull before December 31 to minimize taxes, maximize deductions, and set yourself up for a smoother filing season.

From vehicle deductions and short-term rental timing to real estate professional status, cost segregation, and the latest SALT deduction updates, Thomas and Justin share practical insights for both active and passive investors. They also highlight common pitfalls, like letting the tax tail wag the dog, and explain how to apply these strategies correctly in your own situation.

You’ll learn:

- How to qualify for 100% bonus depreciation on vehicles and real estate in 2025

- What it really takes to lock in short-term rental tax benefits before year-end

- Why REPS qualification is nearly impossible to start from scratch in Q4

- When to complete a cost segregation study (and when it can wait)

- How the updated SALT cap could impact your AGI and deductions

- Key deadlines for 401(k)s, IRAs, HSAs, and paying your kids through your business

- Why bookkeeping and documentation now will save you headaches in tax season

Whether you’re a seasoned investor or just looking to make smart year-end moves, this episode breaks down the most valuable tax strategies for real estate professionals, with clear guidance on how to apply them responsibly and in compliance with the IRS.

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

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 Tax Smart REI Podcast, Thomas Castelli sits down with Matt Hamilton and Nathan Sosa, co-hosts of the Major League Real Estate Podcast and leaders at Hall CPA, to unpack the complex world of real estate syndications and funds and the tax traps that even seasoned operators overlook.

Matt and Nathan work directly with large private equity clients and syndicators, managing tens to hundreds of millions in assets. Together, they break down what it really takes to structure deals, protect investors, and stay compliant when managing other people’s money. From operating agreements to bonus depreciation, this episode reveals why running a syndication isn’t just about raising capital. It’s about running a business the right way.

You’ll learn:

- The key differences between syndications and funds (and how to choose the right structure)

- The biggest mistakes operators make with their operating agreements and tax allocations

- How to avoid costly issues with K-1s, depreciation, and recapture

- What fund managers must know about open vs. closed funds and investor onboarding

- Why choosing the right CPA can protect your reputation and your investors’ returns

Whether you’re an experienced syndicator or just thinking about launching your first fund, this episode is packed with essential insights on how to operate, report, and grow like a professional, without putting your investors or your business at risk.

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

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 Tax Smart REI Podcast, Thomas Castelli sits down with Annette Grant and Sarah Karakaian, co-founders of Thanks for Visiting, to reveal what it really takes to run a profitable short-term rental business in today’s market.

Annette and Sarah have coached thousands of hosts on how to build scalable, hospitality-driven operations that actually make money. Together, they unpack the truth behind STR success, from pricing and KPIs to bookkeeping and mindset, and why short-term rentals are not the “passive income” opportunity many think they are.

You’ll learn:

- The #1 reason most hosts leave money on the table (and how to fix it)

- The five KPIs every short-term rental owner should track

- Why running a short-term rental is running a business, not just owning a property

- How clean bookkeeping and P&Ls protect you in an audit (and keep profits real)

- The right mindset for long-term success and how to balance cash flow, tax savings, and lifestyle goals

Whether you’re managing your first Airbnb or scaling a growing STR portfolio, this episode is packed with real-world advice on how to stop letting emotion drive decisions and start running your short-term rentals like a professional 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

Connect with Thanks for Visiting: https://thanksforvisiting.com/

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 Tax Smart REI Podcast, Thomas and Ryan sit down with short-term rental expert Taylor Jones to break down how investors are transforming ordinary Airbnbs into high-ROI “money machines”, even as the STR landscape becomes more competitive.

Tune in to learn:

- Why data-driven decisions outperform emotion-based investing every time.

- How to identify high-demand markets with built-in traveler traffic and lower risk.

- The amenities and design upgrades (like pickleball courts and pools) that can add $30K–$70K in annual revenue.

- The 4 ROI levers that drive long-term wealth: tax savings, cash flow, principal paydown, and appreciation.

- How to go from zero to under contract in just 32 days and why timing your launch can supercharge returns.

- The smart 2025 strategy: buy now, rebrand later to maximize tax benefits and long-term performance.

Whether you’re looking to buy your first STR or scale a growing portfolio, this episode is a must-listen guide to building a short-term rental business that actually pays you, month after month, year after year.

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

Connect with Eckard Enterprises: eckardenterprises.com/taxsmartrei/

Connect with Taylor: https://strsearch.com/

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 Tax Smart REI Podcast, hosts Thomas Castelli and Ryan Carriere dive into one of the most-requested topics from high-income investors and professionals, W-2 tax strategies.

Tune in to learn:

- Why W-2 income is so highly taxed and the biggest obstacles to offsetting it

- How Section 469 passive activity rules work and proven ways to navigate them with real estate professional status (REPS) or short-term rentals

- How the $626,000 Excess Business Loss (EBL) limit applies to high earners and how to strategically plan around it

- Ways to generate non-passive losses through active businesses and oil & gas investments

- How to stack charitable deductions (like donor-advised funds, CRTs, and CLTs) on top of business losses for maximum impact

- Traditional but powerful tactics, including 401(k)s, HSAs, SALT deductions, and capital loss harvesting

- Which “too-good-to-be-true” tax schemes to avoid and how to spot them before they get you audited

This comprehensive breakdown gives you a complete view of W-2 taxation.

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

Connect with Eckard Enterprises: eckardenterprises.com/taxsmartrei/

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.

From the cockpit to commercial real estate, Tait's story shows how a high-earning W-2 professional can build wealth outside of the stock market. In this episode of the Tax Smart REI Podcast, Tait shares the lessons he learned moving from single-family to multifamily to syndications and the strategies that help pilots and other professionals put their money to work more effectively.

You'll learn:

- How Tait’s early mistakes shaped his investing philosophy

- Why LPs should evaluate sponsors before the deal

- Where commercial real estate sits in today’s cycle

- How oil & gas and STRs can reduce taxes for W-2 earners

- Why access to alternatives in retirement accounts could be a game-changer

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

Connect with Eckard Enterprises: eckardenterprises.com/taxsmartrei/

More From Tait:

Website: https://www.turbinecap.com

Co-authored Oil and Gas eBook:

https://drive.google.com/file/d/17jUYSuoJGCU2ea4SN6MLgazmp-3LE2Lt/view?usp=share_link

Daniel Rusteen's Airbnb book:

https://www.amazon.com/Optimize-Your-Airbnb-audiobook/dp/B07R7CCKPK/ref=sr_1_1?dib=eyJ2IjoiMSJ9.RuqABHwSbg5DlqM7IpdbdyWEN0kpPfMH9Zirre2T_2LGjHj071QN20LucGBJIEps.Twgy40bFLaRKl4w4yOQGk7aOq7kWbEn890lz81_OJDU&dib_tag=se&hvadid=693594071991&hvdev=c&hvexpln=67&hvlocphy=1027744&hvnetw=g&hvocijid=18402973686594528136--&hvqmt=e&hvrand=18402973686594528136&hvtargid=kwd-2430861329715&hydadcr=21936_13365930&keywords=optimize+your+bnb+by+daniel+rusteen&mcid=e22c221c33dd3f379af9461f5fcc2624&qid=1757789681&sr=8-1

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.

Estate planning is one of the most overlooked parts of real estate investing, but without it, your portfolio and family can be left exposed. This week on the Tax Smart REI Podcast, we sit down with attorney, broker, and investor Diana Khan to talk about how real estate investors should approach estate planning.

You'll learn:

- Why every investor needs at least a will and power of attorney (even at 18)

- The difference between wills and trusts, explained with Diana’s “backpack” analogy

- How to decide between revocable and irrevocable trusts

- Practical ways to structure LLCs and holding companies for asset protection

- When (if ever) offshore trusts make sense

- How life insurance ties into your estate plan

Whether you own one rental or a hundred, this episode will show you how to protect your assets, minimize risk, and create a plan that works for your family and your future.

Connect with Diana: https://www.dklawmd.com/

Connect with Eckard Enterprises: https://eckardenterprises.com/taxsmartrei/

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

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.