A real estate investor—we’ll call her Maria—spent 20 years building a $3 million portfolio. She did everything right on paper: maximized depreciation, tracked every expense, and executed 1031 exchanges like a pro. But when sudden health issues forced her to sell everything, she got slammed with a tax bill that wiped out nearly 40% of her gains. The kicker? Most of it could have been avoided with long-term planning.

We’re not tax pros or attorneys—this isn’t personal advice. But it is your warning shot. These are the conversations you need to start now, not when you’re already holding a purchase contract.

Most investors expect capital gains tax when they sell. But you’re actually dealing with four different taxes—and the total can be shocking:

1. Depreciation recapture at up to 25% on every dollar you’ve depreciated. Took bonus depreciation to save money short-term? It’s coming back.
2. Capital gains tax of 0%, 15%, or 20%, depending on your income. Still better than ordinary income—but often avoidable.
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Are you feeling lost when it comes to seeking financial assistance? You're not alone! Many people are struggling to determine who to turn to for help with their finances. Let's clear up the confusion by examining the roles of three key players: the Certified Public Accountant (CPA), the bookkeeper, and the CFP® (CERTIFIED FINANCIAL PLANNER™). Understanding their areas of expertise will empower you to make the right choice for your financial needs. Let's dive in and shed some light on who can best assist you in navigating your financial journey.

A Certified Public Accountant (CPA) is your financial superhero when it comes to your taxes. They're experts at handling taxes, making sure your financial statements are correct, and following compliance. So, basically they’re the ones who need help you in understanding taxes, making sure your money reports are accurate, and making sure you stay on the right side of the Internal Revenue Service.

Think of a Bookkeeper as your financial organizer. They handle your financial records by recording
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