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Category: Tax Benefits

An older woman speaks to a man in a professional setting. Text reads: “Real Estate Professional Status After 55: A Tax Strategy for Doctors.”.

Real Estate Professional Status After 55: A Tax Strategy for Doctors

Many doctors hear about Real Estate Professional Status and immediately assume it does not apply to them. They hear about the time requirements and think, “There’s no way I could do that.” They assume they would need to quit medicine completely. They assume this is something reserved for full-time real estate investors. But for doctors after 55, many of these concerns may no longer apply. As you cut back clinically, move to part-time work, stop taking call, shift to moonlighting, or enter retirement, you begin to get your time back. And when it comes to Real Estate Professional Status, time is not just a lifestyle benefit. It can become a tax-planning advantage. In many ways, REPS seems almost tailor-made for the doctor who is approaching retirement, semi-retired, or already retired. You may have more control over your schedule and more time to devote to rental property investing than you did during the busiest years of your career. My own path looked a little different from what many doctors after 55 may experience, but it shows how powerful it can be to create space for real estate. To qualify for REPS, I cut back clinically and shifted to moonlighting. That is

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A person reviews financial charts with a pen; overlaid text reads, "What is the step-up in basis in real estate? How real estate investors pass wealth tax-free.

What Is the Step-Up in Basis? How Real Estate Investors Pass Wealth Tax-Free

If you ask most real estate investors what their biggest expense is over time, the answer is usually the same: taxes. You pay taxes on rental income. You pay taxes when you sell. And if you’ve owned a property long enough, that tax bill can become substantial—especially once depreciation recapture is factored in. But there’s a lesser-known rule in the tax code that can completely change that outcome. It’s called the step-up in basis, and it’s one of the main reasons real estate has become such a powerful vehicle for building and transferring wealth across generations. What Is “Basis” in Real Estate? To understand the step-up in basis, you first need a basic grasp of what “basis” means. In simple terms, your basis is what the IRS considers your investment in the property. It usually starts as your purchase price, gets increased by improvements, and then reduced over time by depreciation. That number matters because it determines how much tax you owe when you sell. If your basis is low and your property value is high, you’ll owe taxes on that difference. And after years of appreciation and depreciation, that gap can get pretty wide. What Happens to Your Property’s

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A calculator and pen rest on scattered US dollar bills. Text explains how partial asset disposition is a tax-saving strategy for owners of rental and sober living properties.

Partial Asset Disposition: The Overlooked Tax Strategy That Could Save You Thousands

Summary: Partial Asset Disposition (PAD) is a little-known but powerful tax strategy that allows real estate investors to deduct the remaining value of building components—like roofs, HVAC systems, or plumbing—when they’re replaced during renovations. Introduced under the 2014 Tangible Property Regulations, PAD can generate significant deductions in the year of disposal, but it must be claimed correctly and on time. While PAD doesn’t bypass passive loss rules, it can meaningfully reduce taxable income when paired with strategies like cost segregation, REPS, or short-term rentals. Because most CPAs overlook PAD and timing is critical, investors who understand and plan for it can save tens of thousands of dollars and protect themselves from future depreciation recapture. [Disclaimer: We are not accountants, lawyers or financial advisors, so please consult your own team of professionals about the topics covered in this article.] If you’ve ever replaced a roof, HVAC system, or plumbing in one of your rental properties, you may have unknowingly missed out on a powerful tax-saving strategy. It’s called Partial Asset Disposition (PAD) — and if you don’t know what it is, or your CPA hasn’t told you about it, you could be leaving tens of thousands of dollars on the table.

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Two people walking on a path with text overlay about using a Deferred Sales Trust to save on taxes.

How to Use Deferred Sales Trust to Save You on Taxes

[Disclaimer: We are not accountants, lawyers, or financial advisors, so please consult your own team of professionals about the topics covered in this article.]   Are you facing a large capital gain from the sale of a property and looking for a way to defer the capital gains tax? A Deferred Sales Trust (DST) is an alternative to a 1031 exchange that may be a better fit for some real estate investors. A Deferred Sales Trust is a financial tool that allows you to defer paying capital gains taxes when you sell an appreciated asset, like real estate or even a business. Instead of selling your property and getting hit with a huge tax bill, you place it in a trust. The trust then sells the property and spreads out the payments to you over time. This allows you to spread out your tax payments as well. But when should you consider using a DST, and how exactly does it work? Let’s break it down.   When Might a Deferred Sales Trust Be the Right Choice for Real Estate Investors? If you’re a real estate investor, you know the power of deferring taxes—it’s one of the big reasons people love

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Promotional graphic for a blog about tax-saving strategies for real estate investors, featuring CPAs Amanda Han and Matt MacFarland.

How to Use Real Estate to Slash Your Tax Bill with Amanda Han and Matt MacFarland

In this Doctors Building Wealth episode, we sit down with seasoned CPAs and real estate investors Amanda Hahn and Matt McFarland, the minds behind Keystone CPA, who share five powerful tax-saving strategies tailored for real estate investors. If you’re a high-income professional, especially in medicine, looking to reduce your tax burden, this podcast episode is a must-listen.   Amanda and Matt reveal practical, no-nonsense strategies—from structuring short-term rentals for optimal tax benefits and using LLCs effectively to paying your kids (yes, it’s legal!) to maximize deductions. Plus, they cover savvy approaches to leverage “lazy assets” like stocks and retirement accounts, boosting your portfolio without adding hefty tax liabilities. This episode is just a glimpse of the expert insights shared at our 2024 Fast FIRE to Freedom Summit! If you’re ready to dive deeper into wealth-building strategies, tax-saving tips, and expert guidance for a prosperous 2025 and beyond, grab access to the entire four-day Summit replay. You’ll get lifetime access to 16+ hours and learn directly from seasoned investment pros to start taking control of your financial future today! 🎧 Listen to this week’s podcast episode now to discover from Amanda and Matt how to keep more of what you earn, grow passive income, and secure your

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Image of a blog post titled "Real Estate Dealer Status and How to Leverage It for Tax Savings," featuring a piggy bank and calculator in the background.

Real Estate Dealer Status and How to Leverage It for Tax Savings

[Disclaimer: We are not accountants, lawyers, or financial advisors, so please consult your own team of professionals about the topics covered in this article.]   In real estate, tax “status” or “designation” plays a crucial role in determining how income and expenses are treated. One particularly important tax status is that of a real estate dealer, also known as a real estate developer. This status, defined by IRS guidelines and case law, comes with specific tax implications that differ significantly from those applied to real estate investors. Understanding this distinction is essential for anyone involved in frequent real estate transactions, particularly those who flip properties or develop land.   What Is Real Estate Dealer Status? A real estate dealer is defined as someone who holds properties primarily for sale to customers in the ordinary course of business. The IRS looks at individuals or entities engaging in real estate transactions to determine whether they should be taxed as dealers or investors. While an investor holds properties for appreciation and rental income, a dealer’s primary intention is to sell properties for profit.   IRS Factors for Determining Dealer Status The IRS considers several factors when deciding if someone is a real estate

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Text overlay on a teal background: "Understanding Depreciation Recapture in Real Estate Investing." Below, a summary about its importance and strategies to minimize impact. Background shows a calculator.

Understanding Depreciation Recapture in Real Estate Investing

[Disclaimer: We are not accountants, lawyers, or financial advisors, so please consult your own team of professionals about the topics covered in this article.]   Depreciation recapture is a critical concept for real estate investors, particularly when selling a property. While depreciation provides significant tax benefits during ownership, it comes with a catch when it’s time to sell: depreciation recapture. In this article, we’ll explore what depreciation recapture is, how it works, and strategies to minimize its impact.   What Is Depreciation and How Do Investors Benefit? Depreciation is a tax deduction that allows real estate investors to account for the wear and tear on their properties. The IRS recognizes that properties lose value over time due to usage, so it allows investors to deduct a portion of the property’s value from their taxable income each year. In residential real estate (single-family homes, small and large multifamily properties), the depreciation period is 27.5 years, while for commercial properties (e.g., short-term rentals, medical office buildings), it’s 39 years. Investors can further enhance these benefits using accelerated depreciation methods, like cost segregation, which allows them to depreciate certain components of the property faster than the standard timeline. Additionally, bonus depreciation can be

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Suspended Passive Losses: Unlock Them When You Sell

How Selling a Property Unlocks Suspended Passive Losses to Significantly Lower Your Taxes

[Disclaimer: We are not accountants, lawyers, or financial advisors, so please consult your own team of professionals about the topics covered in this article.]  Real estate is one of the most powerful tools for building wealth and reducing taxes, but many investors overlook one of its lesser-known benefits: the ability to unlock suspended passive losses when you sell a property. Whether you’re selling at a gain or a loss, these suspended losses can provide significant tax savings by sheltering various types of income, including non-passive income like W-2 wages. Let’s explore how this works and how you can take advantage of this tax strategy What Are Suspended Passive Losses? Suspended passive losses are essentially tax deductions you’ve accumulated but were unable to use in previous years due to the IRS’s passive activity loss rules. Under IRS Publication 925 (Passive Activity and At-Risk Rules), passive losses typically cannot be used to offset non-passive income, such as W-2 wages or business income, unless certain exceptions are met. Why Passive Losses Get Suspended in the First Place If you don’t qualify for Real Estate Professional Status (REPS) or the short-term rental tax loophole to treat your real estate activities as non-passive, your rental

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