The Legacy Academy

One of the biggest tax misunderstandings in real estate investing isn’t depreciation… and it isn’t deductions.It’s how your profit is classified.In this episode, we explain the critical difference between ordinary income and capital gains and why that single classification can dramatically change how much tax you actually pay when you sell a property.Many investors assume that owning real estate automatically qualifies them for favorable capital gains treatment. In reality, the IRS does not tax real estate based on what you bought, it taxes you based on how you operate.We walk through what determines whether a property sale is taxed at higher ordinary income rates or lower capital gains rates, including how the IRS analyzes investor behavior, holding periods, and intent. Inside this episode, we cover:The legal definition of ordinary income vs. capital gains in real estate investing Episode 10Why house flippers are usually taxed as dealers instead of investorsHow long-term capital gains qualification actually worksThe IRS “dealer vs investor” analysis and the concept of substantial, continuous, and frequent salesHow depreciation and depreciation recapture affect taxable gain Episode 10Why entity structure (LLC, partnership, S-Corp) does not automatically change tax character What documentation investors should keep to support their tax position Episode 10When a long-held property can still be taxed as ordinary incomeHow classification affects eligibility for tax-deferral strategies like 1031 exchanges We also discuss risks many investors don’t realize: If the IRS determines your activity looks like an active real estate business instead of passive investing, your profits may be taxed at significantly higher rates — even if you owned the property for years.This conversation will help you understand how the IRS views real estate activity — and why tax planning needs to start before you buy, not after you sell.🎧 Listen now to learn how the character of your income can determine the success of your investing strategy.

In this episode of the podcast, we break down the most common tax mistakes real estate investors make. Mistakes that quietly destroy cash flow, trigger unnecessary audits, and cost investors tens of thousands of dollars over time.Whether you’re a new investor or have an established portfolio, tax planning mistakes often don’t come from bad intentions, they come from bad assumptions, outdated advice, or treating tax decisions as an afterthought instead of a strategy.We cover real-world issues investors face, including:Choosing the wrong entity structure for rentals or flipsConfusing tax preparation with proactive tax planningFailing to plan for depreciation, recapture, and exit strategiesMixing personal and business expensesRelying on generic CPA advice not tailored to real estate investorsMissing opportunities tied to timing, elections, and asset protectionIgnoring how tax decisions impact probate, estate planning, and legacy goalsThis conversation is especially relevant for:Real estate investorsBusiness ownersHigh-income professionals with rental propertiesAnyone scaling beyond a single propertyWe also explain why “doing it later” is often the most expensive tax decision an investor makes and how proactive planning can legally reduce tax exposure while aligning with long-term wealth and legacy goals.If you’ve ever wondered:“Am I structured correctly for tax purposes?”“Why does my tax bill keep growing even though my portfolio is profitable?”“Is my CPA helping me plan, or just filing returns?”This episode will give you clarity and probably a few uncomfortable realizations.🎧 Listen now to learn how to spot these tax traps before they cost you real money.

What if you could unlock massive tax deductions from your rental property—without qualifying as a Real Estate Professional? That’s the power of the Short-Term Rental Loophole (STRL).In this episode of The Legacy Academy, attorney and tax strategist Natalia Ouellette-Grice, JD, MBA breaks down one of the most powerful and misunderstood opportunities in the tax code for real estate investors. She explains how the IRS treats short-term rentals differently from traditional long-term properties, allowing investors to convert what would normally be passive losses into active deductions.Natalia unpacks the material participation rules that make this loophole work—and the critical mistakes that can cause investors to lose eligibility. She reveals why the rule exists (hint: it was originally written for hotels and motels), how personal use affects qualification, and why even spending more than 14 days in your property could disqualify you.Listeners will also learn how having employees or contractors can jeopardize the loophole if they log more hours on the property than the owner, and what happens when the property is located outside the U.S.—including the limits on bonus depreciation for foreign assets.With her trademark clarity and practical insight, Natalia demystifies this often-misused tax strategy and shows investors how to legitimately leverage it to reduce their taxable income while staying compliant.If you own—or are considering buying—a short-term rental, this episode could be the difference between a costly mistake and a powerful tax advantage.

In real estate, not all income is created equal—and the difference between passive and active can mean thousands of dollars in tax liability.In this follow-up episode of The Legacy Academy, attorney and tax strategist Natalia Ouellette-Grice, JD, MBA continues her deep dive into Section 469 of the Internal Revenue Code, focusing on how investors can transform passive real estate activities into active trades or businesses. She explains the IRS’s default presumption that rental activities are passive, and what it actually takes to overcome that classification through material participation.Natalia walks through the seven material participation tests outlined in the tax regulations and demystifies what truly counts as “active involvement” versus passive oversight. Reviewing financial statements, monitoring operations, or compiling reports for personal use doesn’t make you active—but managing, developing, leasing, or operating your properties does.You’ll also learn which real property activities qualify for Real Estate Professional Status (REPS)—including development, acquisition, and management—and which don’t, such as manufacturing building materials, mining, or agricultural operations. Natalia connects these distinctions to real-world implications, showing how correct classification can unlock deductions, reduce taxable income, and create long-term strategic flexibility for investors.Whether you’re looking to maximize your deductions, qualify for REPS, or simply understand the tax consequences of your business model, this episode delivers the clarity every investor needs to move from passive participant to active wealth builder.

For real estate investors, few tax designations are as powerful—or as misunderstood—as Real Estate Professional Status (REPS) under Section 469 of the Internal Revenue Code. This isn’t just another label. It can determine whether you get to fully deduct your real estate losses against active income or lose those deductions to passive loss limitations.In this episode of The Legacy Academy, attorney and tax strategist Natalia Ouellette-Grice, JD, MBA breaks down exactly what REPS means, how it works, and who truly qualifies. She explains the two-part test that separates serious real estate professionals from passive investors, and why hours logged in qualifying real property activities matter more than most people realize.Natalia explores the common hurdles investors face—especially those with full-time jobs outside real estate—and what the IRS looks for when challenging REPS claims. She also clears up the confusion around married filers: while spouses can share hours for material participation, the taxpayer claiming REPS must still meet the quantitative tests personally.Listeners will also gain clarity on which types of activities—like development, management, or brokerage—count toward qualification, and which don’t. Natalia highlights the real-world tax advantages of earning REPS, such as deducting rental losses in the current year and reducing exposure to the Net Investment Income Tax (NIIT).But she also cautions that REPS isn’t without risk. The documentation burden is heavy, audits are common, and failing to maintain accurate records can turn this tax-saving opportunity into an expensive lesson.If you’re serious about scaling your real estate portfolio or optimizing your tax position, this episode will help you understand when Real Estate Professional Status is worth pursuing—and how to do it right.

The 2026 tax landscape is shaping up to be one of the most consequential years real estate investors have seen in decades. Between proposed limits to 1031 exchanges, tighter IRS audit scrutiny, and shifting rules around depreciation, entity taxation, and estate exemptions, the financial moves you make now could define your long-term wealth strategy.In this episode of The Legacy Academy, attorney and tax strategist Natalia Ouellette-Grice, JD, MBA unpacks the top 10 tax issues that every investor needs to understand before heading into 2026. She dives deep into how accelerated depreciation and cost-segregation studies can create unexpected recapture risks—and how a properly structured 1031 exchange can offset some of those effects when done strategically.Natalia also explores which entity structures—LLCs, partnerships, and trusts—offer the most tax efficiency in the coming year, and how poor recordkeeping can leave investors vulnerable to audit penalties. She breaks down the impact of the upcoming estate-tax exemption changes on generational planning, and why family LLCs may become even more valuable for wealth transfer and protection.Throughout the episode, Natalia highlights real-world mistakes she’s seen investors make—such as misclassifying income, misusing depreciation, or failing to plan around leveraged deductions—and offers practical, legally sound strategies to avoid costly errors. She also sheds light on new audit red flags, including risky deductions, chaotic capital accounts, and misuse of real-estate-professional status.If you own investment property, run an active real estate business, or simply want to make smarter tax moves for the years ahead, this episode will give you the clarity and foresight to protect your profits, minimize risk, and preserve your legacy.

wo investors. Two properties. One massive tax difference. 💸In this episode of The Legacy Academy, attorney and tax strategist Natalia Ouellette-Grice, JD, MBA unpacks the critical tax distinctions between flipping and holding real estate — and why getting this wrong can cost investors thousands.Natalia explains how the IRS decides whether you’re an investor or a dealer, what that means for your tax rate, and how to legally minimize self-employment tax exposure. She also covers depreciation, passive income rules, installment sales, and the latest tax law trends shaping real estate strategies.Whether you’re flipping for quick profits or holding to build generational wealth, this episode gives you the insight you need to plan smarter and protect your returns.💡 In this episode:How the IRS determines if you’re “flipping” or “investing”Why flippers face higher taxes (and how to plan around it)The long-term tax advantages of holding real estateWhat recent tax law updates mean for investors todayIf you want to stop guessing and start structuring your deals with purpose, this episode is your playbook for smarter tax strategy.

Your entity choice can make—or break—your real estate investment strategy. 💼In this episode of The Legacy Academy, attorney and tax strategist Natalia Ouellette-Grice, JD, MBA breaks down one of the most misunderstood (and costly) decisions investors face: choosing the right entity structure. Whether you’re holding rentals, flipping houses, or scaling your real estate portfolio, your tax treatment depends on how you set up your business.Natalia walks you through the real-world differences between LLCs, S-Corporations, and Partnerships, explaining when each makes sense—and when it can become a liability. She covers self-employment taxes, income allocations, distributions, and what happens when you convert or restructure your entity.💡 In this episode:When (and why) to use an LLC taxed as a partnership vs. an S-CorpHow S-Corp rules can hurt real estate investors who buy-and-holdWhat happens when you distribute property—not cash—from your entityHow your structure affects depreciation, capital raising, and 1031 exchangesIf you’ve ever wondered whether you’re using the right entity for your investment strategy, this episode will help you make smarter, tax-efficient decisions that protect your assets and grow your legacy.

Imagine passing real estate to your loved ones—without handing the IRS a massive tax bill. That’s the power of the step-up in basis.In this episode of The Legacy Academy, attorney and tax strategist Natalia Ouellette-Grice, JD, MBA unveils one of the most overlooked wealth-preservation tools in estate planning. She breaks down what the “step-up” actually means, how it works, and how it can save real estate investors hundreds of thousands in capital gains taxes.You’ll learn how valuation works at death, why entity ownership and trusts can complicate eligibility, and which simple mistakes can cause families to lose this benefit entirely. Natalia also shares how proactive estate planning can help investors structure their portfolios to maximize tax efficiency for generations.💡 In this episode:How the step-up in basis resets your property’s taxable valueWhy timing, structure, and documentation matter more than you thinkThe crucial difference between gifting vs. inheriting real estateHow to avoid losing your step-up (and your legacy) through bad planningBecause smart investors don’t just build wealth—they build strategies that outlive them.

When it comes to real estate investing, your basis could be the difference between keeping your profits—or handing them over to the IRS. In this episode of The Legacy Academy, Natalia Ouellette-Grice, Esq., JD, MBA, dives deep into the concept of “basis” — what it really means, how it’s calculated, and why it matters more than most investors realize.From understanding the difference between cost basis and adjusted basis to learning how depreciation, refinancing, and capital improvements affect your bottom line, Natalia breaks it all down in plain English. You’ll also uncover why the step-up in basis can be a massive tax advantage, and what documentation investors must keep to stay audit-ready.Whether you’re flipping, holding, or passing down properties, this episode will help you avoid the costly mistakes that even seasoned investors make when it comes to their tax strategy and long-term wealth.💡 Tune in to learn:How the IRS defines your property’s “true” valueThe right way to track adjustments over timeWhy understanding your basis is key to keeping more of your hard-earned gainsBecause knowing your numbers isn’t just smart—it’s how you protect your legacy.www.lcolawfl.com813-480-2106

Welcome to the latest episode of our podcast, designed specifically for Florida real estate investors! In this enlightening session titled "Tenant's Rights," we delve into the critical aspects of tenant laws in Florida, offering you a comprehensive guide to managing your rental properties effectively and legally. As a real estate investor in Florida, understanding tenant's rights is not just about compliance; it's about creating a harmonious landlord-tenant relationship. This episode is packed with valuable insights that ensure you're well-equipped to navigate the complexities of Florida's rental laws. We cover a range of topics, from security deposit regulations to eviction procedures, ensuring you have the knowledge to protect both your investments and your tenants' rights. Our discussion is led by industry experts who bring years of experience in Florida real estate. They offer practical advice and real-world examples that highlight the importance of staying informed and respectful of tenant's rights. Whether you're a seasoned investor or new to the Florida real estate market, this episode is an invaluable resource for anyone looking to manage their rental properties effectively and ethically. Tune in to "Tenant's Rights: A Florida Real Estate Investor's Guide" to ensure you're not just a successful investor, but a responsible and law-abiding landlord. Empower yourself with the knowledge to foster positive tenant relationships while safeguarding your investment. Don't miss this opportunity to become a more informed and conscientious real estate investor in Florida. Listen now!

Welcome to another insightful episode of our podcast, where we delve into the often-overlooked realm of surplus funds in the context of tax deed and foreclosure sales. Join us as we unravel the mysteries behind surplus funds, a topic that is crucial yet not widely understood by many real estate investors. In this episode, we start by defining what surplus funds are, breaking down the concept into simple terms for our listeners. We explore how these funds are generated, particularly in the aftermath of tax deed and foreclosure sales. Surplus funds can sometimes appear complex, but our discussion aims to demystify them, making the information accessible to both seasoned investors and newcomers to the real estate world. We also shed light on the specific circumstances under which real estate investors might be entitled to surplus funds. This part of the conversation is particularly important, as it reveals opportunities that many investors might be missing out on. We provide practical advice on how to identify and access these funds, ensuring our listeners are well-equipped with knowledge to enhance their investment strategies. Throughout the episode, we use real-life examples and expert insights to paint a clear picture of the process and potential benefits of tapping into surplus funds. Whether you're looking to expand your investment portfolio or just starting out in the real estate industry, this episode is packed with valuable information that could significantly impact your investment decisions. Don't miss out on this opportunity to learn about the hidden potentials in tax deed and foreclosure sales. Tune in to our "Surplus Funds" episode and discover how to maximize your returns in real estate investments by understanding and utilizing surplus funds effectively. Remember to subscribe to our podcast for more insightful episodes like this, and if you find our content helpful, please leave us a review. Your feedback helps us grow and continue providing valuable content for our listeners.

Join us in this insightful episode of our podcast where we delve into the world of Land Trusts with our expert attorney, Natalia Ouellette-Grice. With her profound expertise in Florida Real Estate Law, Natalia demystifies the concept of Land Trusts, a vital tool for real estate investors. In this episode, "Land Trusts: A Key Tool for Real Estate Investors," Natalia unravels the complexities surrounding land trusts, explaining in a clear and approachable manner what they are and how they function. She also sheds light on the various ways land trusts can be a game changer for your real estate investments. Whether you're a seasoned investor or just starting out, this episode is packed with invaluable insights. Don't miss out on this opportunity to learn from one of the best in the business. Whether you're looking to protect your assets, maintain privacy in property ownership, or simply want to explore new investment strategies, this episode is for you. Tune in to gain a wealth of knowledge and empower your real estate investment journey with Natalia Ouellette-Grice.

In this insightful episode of our podcast, we delve deep into the world of Joint Venture Agreements (JVAs) with our expert attorney, Natalia Ouellette-Grice. With her extensive background in Florida Real Estate Law, Natalia breaks down the complexities of JVAs, making them accessible to everyone from seasoned entrepreneurs to first-time investors. Join us as Natalia explains the nuts and bolts of what JVAs are and how they operate in the dynamic landscape of real estate. She offers valuable insights into the essential components of these agreements, ensuring you understand every facet before diving in. Natalia's expertise shines as she highlights the key aspects to watch out for, helping you navigate potential pitfalls and make informed decisions. Whether you're considering a joint venture or simply curious about the intricacies of these collaborations, this episode is a treasure trove of knowledge. Natalia's empathetic and kind approach, combined with her natural ability to teach, makes complex legal concepts approachable and engaging. Don't miss this opportunity to learn from one of the best in the business about protecting your interests in joint venture agreements. Tune in to gain a wealth of information and advice from Natalia Ouellette-Grice, a name synonymous with expertise in business planning and estate planning, as she guides us through the world of JVAs with clarity and depth. This episode is not just a learning experience; it's an essential guide for anyone looking to venture into the realm of joint ventures.

In this insightful episode of the Legacy Academy Podcast, titled "Corporate Transparency Act," our esteemed attorney Natalia Ouellette-Grice delves into the intricate details of the Corporate Transparency Act (CTA) and its significant impact on real estate investors. With her extensive expertise in business and estate planning, Natalia offers a comprehensive understanding of the CTA, providing clarity on this complex legislation. Listeners will gain a thorough understanding of what the CTA entails and why it's crucial for real estate investors. Natalia expertly explains the necessity for reporting to the Financial Crimes Enforcement Network (FinCEN), outlining what specific information needs to be disclosed. This episode is particularly valuable as it sheds light on the legal implications and potential penalties for non-compliance with the CTA. Whether you're a seasoned investor or new to the real estate market, this episode is a must-listen for anyone looking to stay informed and compliant with the latest regulations. Join Natalia as she guides you through the intricacies of the CTA, equipping you with the knowledge to protect your investments and navigate these new legal waters confidently. Tune in to this episode of the Legacy Academy Podcast for an enlightening discussion that blends legal expertise, practical advice, and a deep understanding of the real estate investment landscape.

Join us as we discuss effective networking strategies specifically tailored for real estate investors. Greg Simpson opens up about his personal journey in the real estate realm and sheds light on the transformative impact networking has had on his career. Discover the numerous benefits of cultivating a strong network and gain actionable tips on how to make meaningful connections both online and offline. Greg guides us through the maze of where to find the most valuable networking opportunities, whether it's local meetups, industry conferences, or online platforms. He delves into the art of building relationships that go beyond superficial interactions, and offers advice for introverted individuals looking to thrive in networking environments.

Explore the impact of bankruptcy on investors who have purchased properties at foreclosure auctions in this gripping episode of 'The Legacy Academy.' Join us as we delve into the complexities of bankruptcy declarations and how they affect real estate investors' investments, strategies, and financial future.

Delve into the transformative impacts of the 1985 Supreme Court decision, "Johnson v Davis," on Florida's real estate market in this episode of "The Legacy Academy" podcast. This landmark ruling mandated disclosure requirements when selling real estate, reshaping buyer-seller dynamics and influencing property values and market practices throughout the state. Uncover the legal intricacies and practical ramifications of the decision, as it continues to shape property transactions and buyer protections in Florida today. Join us as we explore how "Johnson v Davis" has left a lasting legacy on the Sunshine State's real estate landscape.

Discover the intricacies of partition suits and gain valuable insights for real estate investors in this episode. Learn how the partition process works and explore the essential steps investors need to take for a successful outcome. Our expert real estate attorney provides comprehensive guidance, from evaluating risks and rewards to preparing a strong case and working with specialized attorneys. Discover negotiation strategies, alternatives to court proceedings, and anticipate potential challenges along the way. Whether you're a seasoned investor or new to the market, this episode equips you with the knowledge and tools to navigate partition suits effectively. Tune in to gain a competitive edge and ensure success in your real estate investment journey. Natalia's Books: Florida Tax Deeds Florida Foreclosures Business Ownership Florida Rentals

In this episode, we provide valuable insights for landlords who have encountered challenges with tenant selection and offer practical advice on how to attract better tenants. Our expert real estate attorney discusses the importance of thorough background checks, effective marketing strategies, and understanding legal considerations while screening tenants. Learn about key criteria and red flags to look for in rental applications, and assess a tenant's responsibility and compatibility. Discover proactive measures to attract desirable tenants and foster positive landlord-tenant relationships. If you're a landlord seeking to improve your tenant selection process, join us for expert tips and best practices that will help you find the right tenant for your rental property. Find Natalia's Book on Amazon! How to Manage Florida Rentals and Win in Court: In Less Time with Less Conflict