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Today’s episode dives into a question many new investors wrestle with: Should you buy a long-term rental or take a swing at a short-term vacation rental? Sandy, who’s currently working with my team, reached out for guidance as she and her partner prepare to purchase their first investment property in Florida. While long-term rentals offer predictability and stability, short-term rentals can deliver eye-popping cashflow—sometimes two, three, even four times more. But as we explore in this conversation, those higher returns come with trade-offs: unpredictable occupancy, increased expenses, constant turnover, potential regulatory headaches, and more hands-on management. I break down the pros, cons, risks, and realities of short-term rentals, contrast them with tried-and-true long-term strategies, and share why I personally stay on the long-term side of the fence. If you’re weighing your options or considering stepping into the vacation-rental world, this is an episode you won’t want to miss.

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Throwback Thursday Episode (The episode originally took place in the year 2020)

This episode is part of our Throwback Series and may include references to older content such as web classes, events, promotions, or links that are no longer active or available. While the conversation and insights still hold value, please note that some information may be outdated.

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If you missed our last episode, be sure to listen to The Hidden 1031 Strategy: How to Buy a Duplex at a Discount and Grow Your Portfolio Fast

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