In this episode of the Tax Smart REI podcast, Thomas and Ryan explore the critical nuances of personal use days for short-term rental properties, a topic that generates frequent questions from their community of real estate investors and tax-savvy listeners. They break down the 14-day rule, share actionable strategies to avoid common pitfalls, and provide clarity on how personal use impacts your tax benefits—especially for those leveraging the short-term rental loophole. Here’s what they discuss: - The 14-day rule and how it applies to short-term rental properties - What counts as personal use and how the IRS defines it - Travel days, family stays, and the gray areas of personal use - Best practices for keeping credible time logs & avoiding audit risks To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Visit PURE at: rentpure.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 are joined by Heather and Isaac from FinCEN Filing Agents to dive deep into the 2024 Corporate Transparency Act (CTA) and what it means for real estate investors and small business owners. They cover: - An overview of the Corporate Transparency Act - Key reporting requirements for LLCs and other entities - The penalties for non-compliance - Insights into exemptions, reporting updates, and the timeline for new and existing entities - Strategies for streamlining the filing process - Privacy concerns and how your information is safeguarded when filing under the CTA File your BOI Reports Today: https://tinyurl.com/Brandon-Hall To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Register for the Year-End Tax Impact Event: go.therealestatecpa.com/3zVWP7E Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Checkout 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 dive into real estate tax strategies by addressing audience questions from their public community and Facebook group. Covering crucial topics, they guide listeners through the complexities of tax planning, especially for short-term rental owners, and how they can leverage tax rules to minimize liabilities. Here’s what they discuss: - Understanding when to use Schedule C vs. Schedule E - Short-term Rental Loopholes and Real Estate Professional Status - Travel, Meal, and Home Office Deductions - Year-End Moves & Capital Gains Strategies To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Register for the Year-End Tax Impact Event: go.therealestatecpa.com/3zVWP7E Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Checkout 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 are joined again by Troy Eckard of Eckard Enterprises to conclude our oil & gas series with a real-world case study on oil and gas working interests. They cover: - A detailed breakdown of a case study involving a working interest investment, including cost structures, potential pitfalls, and strategies for maximizing returns. - How to evaluate investment deals to avoid common mistakes, including understanding the true costs and potential revenue from drilling. - The impact of modern drilling technologies on reducing risk and improving success rates for working interest investors. - How to approach oil and gas as a long-term investment strategy that can generate ongoing cash flow while leveraging substantial tax benefits. - And much more! If you’re looking for ways to diversify your portfolio with alternative investments, this episode is packed with real-world oil & gas insights. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Register for the Year-End Tax Impact Event: go.therealestatecpa.com/3zVWP7E Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Checkout 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 break down year-end tax strategies tailored for real estate investors, providing valuable insights for maximizing tax savings before the year ends. Here’s what they cover: - The advantages of buying a short-term rental before year-end and how to qualify for the short-term rental loophole. - Maximizing vehicle deductions, including the benefits of buying a vehicle with a gross weight of 6,000 pounds or more. - Key strategies like cost segregation timing and real estate professional status. - Common but crucial year-end tax tactics like prepaying expenses, bookkeeping, and tax loss harvesting. - The importance of ensuring you have W9s from contractors and reviewing your entity structure. If you’re looking for more actionable tax strategies to implement before the end of the year, register for our Year-End Tax Impact event here: go.therealestatecpa.com/3zVWP7E To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Checkout 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 are joined by renowned analyst and housing expert, Logan Mohtashami, to explore the current state of the housing market, interest rates, and what might be in store for 2025. They cover: - Logan's insights into the factors driving mortgage rates, including the crucial role of labor data and the Federal Reserve's policies. - A detailed discussion on supply and demand dynamics in the real estate market and how they impact pricing. - Potential interest rate cuts and economic trends affect real estate demand and affordability. - What investors should consider when navigating today's housing market, including demographic shifts and regional trends. - And much more! Whether you're a real estate investor, homeowner, or simply curious about the future of the housing market, this is an episode you don’t want to miss. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Register for the Year-End Tax Impact Event: go.therealestatecpa.com/3zVWP7E Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Checkout 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 Tax Smart REI episode, Ryan is joined with Nathan Sosa, a Senior Tax Advisor at Hall CPA to dive into a new court case related to real estate professional status. This continues to be a heavily audited topic and with additional IRS funding, the audits will only increase from here. If you're curious about what factors led to this taxpayer losing in court and what they could have done differently, don't miss this episode. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Get the Top 8 Mistakes Real Estate Investors Make: go.therealestatecpa.com/3ygHVrJ Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Learn more about Property Llama: www.propertyllama.com/taxsmart Court Case: https://www.therealestatecpa.com/blog/tax-court-denies-real-estate-professional-status-for-carriage-house-investor Checkout 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 is joined by frequent guest, Justin Shore, EA for the go-to guide to real estate investment strategies. They break down each strategy, the tax benefits, and the implications. Topics include: - The tax advantages of direct ownership and how to maximize deductions. - The differences between long-term and short-term rentals and the operational and tax considerations. - Syndicates and funds, REITs, and DSTs as passive investment vehicles, their liquidity, and tax strategies. - How investment strategies like the BRRRR method and the 1031 exchange can impact your tax liabilities. - The importance of aligning your investment goals with the right strategy. Whether you’re a hands-on investor or prefer a more passive approach, this is the episode you want to listen to over and over. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Get the Top 8 Mistakes Real Estate Investors Make: go.therealestatecpa.com/3ygHVrJ Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Learn more about Property Llama: www.propertyllama.com/taxsmart Checkout 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 is joined by Isabelle Guarino to discuss investing in residential assisted living facilities. Isabelle shares her personal journey into the space and explains how this business model can generate significant cash flow. Listen now to learn: - The steps to owning and operating these facilities—or just leasing them to an operator. - The financial and tax opportunities that come with this growing sector. - How you can get started and scale your senior assisted living investment. Whether you're looking for high cash flow or want to create a long-term wealth-building strategy, this episode offers valuable insights for real estate investors. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Get the Top 8 Mistakes Real Estate Investors Make: go.therealestatecpa.com/3ygHVrJ Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Learn more about Property Llama: www.propertyllama.com/taxsmart Checkout Thomas's new YouTube channel: www.youtube.com/@thomascastelli Connect with Isabelle: https://www.ral101.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.

In this episode of the Tax Smart REI podcast, Thomas Castelli and Nathan Sosa explore the often overlooked Section 179 deduction and its potential benefits for commercial real estate investors and short-term rental owners. As bonus depreciation phases out, Section 179 is becoming more relevant for those looking to immediately expense certain capital expenditures. You’ll learn: - How to strategically use Section 179 to offset W-2 income - The limitations when held in partnerships - The recapture implications investors need to be aware of. Whether you’re a seasoned commercial real estate investor or getting started with short-term rentals, this episode will help you navigate the complexities of this tax strategy. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Get the Top 8 Mistakes Real Estate Investors Make: go.therealestatecpa.com/3ygHVrJ Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Learn more about Property Llama: www.propertyllama.com/taxsmart Checkout 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 is joined by financial advisor Nathan Cook to discuss a powerful strategy for real estate investors: using equity losses from the stock market to offset real estate capital gains through a process called active indexing. They cover key topics such as: - The fundamentals of tax loss harvesting and how it benefits real estate investors. - Active (or direct) indexing and how it differs from traditional ETFs. - How to use equity losses to reduce or eliminate capital gains on your real estate sales. - The role of technology in simplifying direct indexing and maximizing returns. - Who should and shouldn’t consider this strategy based on portfolio size and investment goals. Whether you're a real estate purist or an investor with a diversified portfolio, this episode will provide you with another tax-saving strategy to enhance your wealth-building journey. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Get the Top 8 Mistakes Real Estate Investors Make: go.therealestatecpa.com/3ygHVrJ Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Connect with Nathan: [email protected] https://x.com/Nathan_C_Cook Learn more about Property Llama: www.propertyllama.com/taxsmart Checkout Thomas's new YouTube channel: https://www.youtube.com/@thomascastelli Any opinions are those of Nathan Cook and not necessarily those of Raymond James. The information has been obtained from sources considered to be reliable, but we do not guarantee that the foregoing material is accurate or complete. Any information is not a complete summary or statement of all available data necessary for making an investment decision and does not constitute a recommendation. Expressions of opinion are as of this date and are subject to change without notice. This information is not intended as a solicitation or an offer to buy or sell any security referred to herein. Investments mentioned may not be suitable for all investors. There is no guarantee that these statements, opinions or forecasts provided herein will prove to be correct. Past performance may not be indicative of future results. Investing involves risk and you may incur a profit or loss regardless of strategy selected..Raymond James and its advisors do not offer tax or legal advice. You should discuss any tax or legal matters with the appropriate professional. The S&P 500 is an unmanaged index of 500 widely held stocks that is generally considered representative of the U.S. stock market. Keep in mind that individuals cannot invest directly in any index, and index performance does not include transaction costs or other fees, which will affect actual investment performance. Individual investor's results will vary. Raymond James and its advisors do not offer tax or legal advice. You should discuss any tax or legal matters with the appropriate professional. 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.