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 estat...

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an established portfolio, tax planning mistakes often don’t come from bad intentions, they come from bad assumptions , outdated ad...

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...

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...

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 , attorn...

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...

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 yo...

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 treatm...

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...

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...

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...

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...

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 surrou...

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...

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 cla...

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 of...

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 pract...

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. D...

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...

Navigating possession issues can be complex, and different acquisition circumstances require varying approaches. Our expert hosts will delve into the intricacies of gaining possession, providing valuable insights tailored specifically for real estate investors.   Learn about the essential notices and legal requirements involved in obtaining possession of an investment property. We will discus...

Understanding when and how to back out of a real estate contract is crucial for investors seeking flexibility and protection in their investment ventures. Our expert hosts will shed light on the situations that may allow you to exit a contract without significant repercussions, ensuring you are well-informed and empowered to make the right decisions. We'll discuss various options available to inve...

Lease agreements form the foundation of successful landlord-tenant relationships, and understanding their intricacies is vital for real estate investors. Natalia brings her expertise and experience to the table, guiding listeners through the fundamentals of lease agreements and shedding light on common misconceptions that can lead to costly mistakes. In this episode, you will learn the key compone...

In this episode of "The Legacy Academy" podcast, we delve into the fascinating world of tax deeds and vacant land investments. Our special guest, Aaron Kinder, the owner of Florida Wholesale Land and an experienced investor in vacant land, joins us to share his invaluable insights and boots-on-the-ground experience in this niche market.   Join us as we explore the potential and opportunities...

Join us for an informative episode of our podcast as we dive deep into the world of foreclosures and due diligence. Designed specifically for real estate investors who participate in foreclosure auctions, this episode is packed with valuable insights and practical tips to help you make informed investment decisions. Natalia Ouellette-Grice, is an esteemed author who has written a book titled "Flor...