In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with Travis and Regan Perry, real estate investors who have crafted a flourishing portfolio of short-term rental properties. With roots in Iowa, the Perrys share their journey from purchasing their first home to managing multiple properties across several states. Tune in to learn: - Steps to start investing in short-term rentals and build a substantial property portfolio. - How to leverage local events and tourism to maximize rental income. - The importance of tax strategies, including cost segregation, to enhance cash flow. - Practical tips for managing properties remotely and building a reliable team. Whether you’re a budding entrepreneur or an experienced investor, this episode is brimming with invaluable insights and inspiring stories to help you expand your real estate ventures. 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 Connect with Travis & Regan: https://shorttermrentaledge.com/ https://perrydisevacationrentals.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 of the Tax Smart REI Podcast, Thomas & Ryan sit down with Stacey Dowling, a seasoned mortgage lender specializing in short-term rental financing. Stacey brings over 30 years of experience to the table, offering actionable insights into obtaining loans for short-term rentals. Tune in to learn: - How to qualify for a short-term rental loan. - The impact of tax returns, depreciation, and cost segregation on lending decisions. - Strategies to navigate regulations and mitigate challenges from neighbors or local laws. - Creative approaches like midterm rentals to adapt to changing market dynamics. Whether you’re a seasoned investor or just getting started, this episode is packed with expert advice and real-world examples to help you achieve your real estate goals. 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 Connect with Stacey Dowling: Email: sdowling@dg-lending.com Visit PURE at: www.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 Ben Fraser, Chief Investment Officer of Aspen Funds and host of the Invest Like a Billionaire podcast, to explore strategies of the ultra-wealthy and how they invest differently. They cover: - The difference between ultra-high-net-worth investors and retail investors - Why private markets, including real estate and private equity, are the cornerstone of billionaire investment strategies - The trade-offs between active and passive real estate investing - Key insights on evaluating sponsors and deals to avoid common pitfalls - Emerging trends in the alternative investment space - And much more! If you’re curious about how the wealthiest individuals protect and grow their capital—and how you can apply those strategies—this episode is full of actionable insights. 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: www.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 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.

Heather Lucor, CEO of FinCEN Filing Agents, shares crucial insights about the Corporate Transparency Act and its looming 2024 implications for real estate investors and small businesses. She explains key reporting requirements and the dire consequences of non-compliance. The conversation highlights strategies to streamline the filing process, the importance of timely updates, and privacy concerns regarding sensitive information. Lucor also addresses the alarming low filing rates and offers solutions for those feeling overwhelmed by the upcoming deadlines.

Discover essential tax strategies for short-term rental owners, including the differences between Schedule C and Schedule E. Learn about maximizing deductions on travel, meals, and home offices. Explore capital gains strategies and how to minimize tax liabilities using Qualified Opportunity Zones. Delve into the long-term tax benefits of losses offsetting future profits and the importance of accurate record-keeping. Plus, get tips on navigating potential IRS audits and year-end tax planning!

Troy Eckard, an oil and gas expert with over 40 years of experience, shares his invaluable insights on working interests. He discusses a detailed case study that highlights cost structures and common pitfalls in investing. Troy emphasizes the importance of modern drilling technologies in reducing risks and maximizing returns. He also explores the long-term investment potential of oil and gas, showcasing substantial tax benefits that can diversify portfolios. His practical strategies and due diligence tips are essential for anyone considering this sector.

Explore savvy year-end tax strategies specifically designed for real estate investors. Learn about the benefits of purchasing short-term rentals and how to leverage the short-term rental loophole. Discover ways to maximize vehicle deductions, especially for heavier vehicles. Gain insights on qualifying for real estate professional status and the importance of cost segregation. Plus, find out how to effectively implement tax loss harvesting, prepay expenses, and ensure proper documentation for contractors to boost your deductions before the year closes.

Logan Mohtashami, a renowned housing analyst, dives deep into the dynamics of the current real estate market. He discusses how mortgage rates are influenced by labor data and Federal Reserve policies. The podcast highlights the impact of supply and demand on pricing and potential interest rate cuts that could reshape market affordability. Logan also shares insights on demographic shifts affecting housing demand and provides strategies for investors navigating today’s challenging market conditions.

Nathan Sosa, a Senior Tax Advisor at Hall CPA, shares his expertise on real estate tax strategies and IRS scrutiny. He delves into a recent court case highlighting the complexities of obtaining real estate professional status, especially when balancing a W-2 job. Key takeaways include the importance of documentation and education to avoid costly mistakes during audits. Sosa also discusses strategies for short-term rental investments and the critical need for professional guidance in navigating evolving tax laws.