Tax Smart Real Estate Investors Podcast

Former cancer researcher Becky Nova transformed financial hardship into a thriving real estate portfolio spanning New York and the Dominican Republic.

In this episode, Becky shares how she went from losing over $100,000 in a failed business overseas to building a 17-door portfolio through house hacking, strategic acquisitions, and remote property management.

In this episode, we cover:

- How Becky house hacked her first duplex in Yonkers

- Scaling to 17 units across multiple markets

- Investing in the Dominican Republic remotely

- Building systems for self-managing rentals

- Why she avoids “hot markets” from social media lists

- Tax strategy lessons from working with multiple CPAs

- The rise of the Lady Landlords community

- Real estate investing as a path to financial independence

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

Register for the FREE Investing Debate: go.therealestatecpa.com/debate

Submit your question for Tom & Nathan: go.therealestatecpa.com/question

Join Lady Landlords: https://www.facebook.com/groups/LadyLandlords/

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 Major League Real Estate Podcast, Nate Sosa and Thomas Castelli break down what happens when experienced CPAs integrate directly with syndicators and fund managers.

Topics Covered:

- Common operating agreement tax mistakes

- Entity structuring and partnership considerations

- K-1 season expectations and extension strategies

- 1031 exchanges, refinance considerations, and exit planning

- How to choose the right CPA for your syndication business

Most syndicators think their CPA’s job starts and ends with filing partnership tax returns and sending out K-1s. But in reality, the right CPA should function as a strategic partner throughout the entire lifecycle of your deal.

Request a free discovery meeting: go.therealestatecpa.com/mlre

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.

Can you legally pay your children through your business and use it to build tax-free wealth for their future?

In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nate Sosa break down one of the most powerful family tax strategies available to business owners and real estate investors.

You’ll learn:

- How to legally pay your kids through your business

- The entity structures required to avoid payroll taxes

- What jobs children can reasonably perform

- How much you can realistically pay them

- Roth IRA strategies for children

- Trump Accounts vs. 529 Plans

If you're a real estate investor or business owner with kids, this episode could completely change how you think about family wealth building and tax planning.

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

Register for the FREE Investing Debate: go.therealestatecpa.com/debate

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.

In this episode of the Major League Real Estate Podcast, Nate Sosa and Thomas Castelli sit down with securities and real estate attorney Mola Bosland to break down the legal and strategic side of real estate syndications.

Mola shares how successful syndicators structure their entities, when to use a 506(b) vs. 506(c), the biggest mistakes new operators make when raising capital, and why investor trust matters more than flashy projections.

The conversation also dives into fund structures, private equity partnerships, preferred returns, investor relations, and the growing institutionalization of real estate investing.

Whether you’re raising capital for your first deal or scaling into larger funds and family office partnerships, this episode is packed with actionable guidance to help you stay compliant, protect investors, and grow sustainably.

Request a free discovery meeting: go.therealestatecpa.com/mlre

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.

What happens when you sell a rental property after taking depreciation deductions?

Many investors are shocked to learn they may owe more than just capital gains tax.

In this episode, Thomas Castelli and Nate Sosa break down how depreciation recapture actually works, including the three different tax “buckets” investors need to understand: Section 1245 recapture, unrecaptured Section 1250 gain, and Section 1231 capital gains.

They explain how bonus depreciation, cost segregation studies, and qualified improvement property impact your taxes when you sell and why accelerated depreciation can still make sense despite future recapture.

If you own rental properties, short-term rentals, or commercial real estate, this episode will help you understand what taxes to expect when exiting a deal and how to plan ahead to minimize them.

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.

Should your real estate syndication use an S corporation, a C corporation, or an LLC taxed as a partnership? In this episode, Thomas Castelli and Nate Sosa break down the real tax implications behind entity structuring for syndicators, fund managers, and passive investors.

They explain why LLCs taxed as partnerships are typically the gold standard for real estate syndications, where S corps can accidentally limit depreciation benefits, and how C corps can create double taxation problems that investors often overlook.

You’ll also learn:

- Why depreciation and debt allocation matter so much in syndications

- The hidden limitations of S corps for real estate investors

- When a C-corp blocker actually makes sense

- How GP entities and management companies should be structured

- The biggest mistakes syndicators make before raising capital

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.

In this Q&A episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa answer real questions from listeners, clients, and the Tax Smart community.

They cover a wide range of topics, from how to properly track your time for material participation, to how short-term rentals should be classified for tax purposes, to what really qualifies for bonus depreciation under the latest tax law changes.

They also break down strategies for investing for your kids’ future, including 529 plans, Roth IRAs, and newer account options, along with the pros and cons of each.

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

Time Log: https://www.therealestatecpa.com/time-log/

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 Major League Real Estate Podcast, we break down everything you need to know about 1031 exchanges and why they get complicated fast when syndications are involved.

We cover:

- Why you can’t directly 1031 into a syndication

- The biggest issues GPs and LPs run into when trying to defer taxes

- Workarounds like Delaware Statutory Trusts (DSTs) and Tenants-in-Common (TIC) structures

- Advanced strategies like drop-and-swap and how to plan for them on the front end

- Common pitfalls including boot, debt replacement, and IRS scrutiny

We also cover practical advice for syndicators, like how to structure deals upfront if you want to offer 1031 optionality, and what investors should look for when trying to defer gains into their next opportunity.

Whether you're an active investor, passive LP, or syndicator, this episode will help you understand how to properly navigate 1031 exchanges without blowing up your deal or your tax strategy.

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.

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.

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.