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.

In this episode of the Tax Smart REI Podcast, Thomas Castelli and Ryan Carriere, CPA, answer real investor questions from the investing community, tackling some of the most pressing topics around bonus depreciation, short-term rentals, and advanced tax planning.

Tune in to learn:

- How cost segregation results differ between condos, single-family homes, and properties with big-ticket land improvements like pools

- Why new renovations on older rentals may still qualify for 100% bonus depreciation under the latest rules

- The nuances of converting a personal residence into a short-term rental, and when only 40% bonus depreciation applies

- The pros and cons of using Form 3115 to catch up missed depreciation—and why DIY may not be the best option

- Key IRS rules around ADUs, STR participation, and what really triggers depreciation recapture

This Q&A-style episode delivers practical answers to questions investors are asking right now in 2025.

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

Get your FREE ticket to the 2025 Tax, Legal, and Wealth Summit:

www.taxandlegalsummit.com/registration

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 and Ryan Carriere, CPA, break down the two most common questions investors are asking after the passage of the “Big Beautiful Bill” and the return of 100% bonus depreciation:

- Should you invest in real estate or specifically short-term rentals for tax savings?

- When does it make sense to start working with a tax strategist?

Tune in to learn:

- Why existing landlords who haven’t done tax planning may be leaving money on the table

- How to decide if short-term rentals make sense for your goals, lifestyle, and time commitment

- A step-by-step framework for estimating your first-year tax savings using bonus depreciation

- The reality of material participation, hours required, and capital needed to get started

- When to engage a tax strategist if you’re already in the game or just getting started

- Why time is running short in 2025, and how late you can still implement this strategy

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

Get your FREE ticket to the 2025 Tax, Legal, and Wealth Summit:

www.taxandlegalsummit.com/registration

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 Hall CPA Advisory Manager Justin Shore to break down why bookkeeping isn’t just busy work, it’s the foundation of audit defense and financial success as a real estate investor.

Tune in to learn:

- Why sloppy bookkeeping can raise red flags and trigger IRS scrutiny

- The key differences between Schedule E and Schedule C—and why they matter for your rentals

- How proper categorization of expenses (like cleaning vs. repairs) can make or break your audit defense

- Why bank statements aren’t enough, and the documentation you must keep to substantiate deductions

- The penalties and costs of poor records and how to avoid them

- The line between bookkeepers and tax preparers, and what responsibilities truly fall on you

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

Get your FREE ticket to the 2025 Tax, Legal, and Wealth Summit:

www.taxandlegalsummit.com/registration

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 and Ryan sit down with financial planner and short-term rental investor Zack Mattos to unpack how he went from a 20-year career focused solely on traditional retirement accounts to leveraging real estate to nearly eliminate his tax bill, including a staggering $943K in depreciation from one luxury rental property.

Tune in to learn:

- How he turned his Austin dream home into a high-income rental and tax-saving machine

- The cost segregation strategy that generated nearly $1M in depreciation in a single year

- Why he paused retirement account contributions to focus on real estate acquisitions

- How REP status transformed his tax outcomes and influenced client recommendations

- The S-corp move and family payroll strategy that added tens of thousands in annual savings

- His plan to build a portfolio of luxury rentals in one high-demand neighborhood for scale and ease of management

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

Get your FREE ticket to the 2025 Tax, Legal, and Wealth Summit:

www.taxandlegalsummit.com/registration

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

go.therealestatecpa.com/41JuQBX

Connect with Zack: https://www.zackmattos.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 entrepreneur and investor John Paul Houston to unpack his journey from running a backyard chicken operation to building a $3.5M private lending portfolio and a 100+ door real estate empire — all while dramatically reducing his tax bill by qualifying as a Real Estate Professional.

Tune in to learn:

- How John went from semi-retirement to scaling multiple income-producing businesses

- Why he shifted from passive lending to active investing for greater returns and tax benefits

- The REP strategies and depreciation plays that helped him save big on taxes

- How he structures equity incentives to retain top talent and transfer ownership

- Why West Virginia is his secret weapon for finding 12-cap multifamily deals with minimal red tape

- The role private lending plays in his long-term diversification and estate planning

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

Get your FREE ticket to the 2025 Tax, Legal, and Wealth Summit:

www.taxandlegalsummit.com/registration

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.