3 Cash-Flowing Real Estate Deals in 2025 (& Where We Found Them)

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May 26, 2025

Garrett Brown, a short-term rental expert and host of the BiggerStays YouTube channel, joins Ashley Kehr, co-host of Real Estate Rookie, to explore real estate investment opportunities in 2025. They analyze three cash-flowing properties, comparing long, medium, and short-term rental strategies. Discover why short-term rentals might not always be the most profitable option and learn about innovative tactics like renting-by-the-room and subdividing lots for extra cash flow. Regulations on short-term rentals could actually benefit investors too!

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INSIGHT

Short-Term Rental Profit Levers

Short-term rental profitability depends heavily on purchase price and added amenities.
Operational improvements can significantly increase revenue beyond baseline projections.

ADVICE

Analyze Multiple Rental Strategies

Analyze rental properties using short, mid, and long-term strategies from day one.
Ensure exit strategies by confirming viability across different rental approaches, especially for beginners.

INSIGHT

Long-Term Rental Cost Challenges

Mortgage payments and other costs often exceed rental income in long-term rental scenarios.
Long-term rents may not cover monthly expenses, making some deals unprofitable without adjustments.

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There are still real estate deals even in 2025. To prove it, we’re taking three real (on-market!) deals and analyzing them three ways: as a long, medium, and short-term rental to see which will have the highest cash flow. All of these properties are around or under the median home price in the US and have at least one strategy that makes them profitable, even in 2025 with today’s high interest rates.

To help run the deal analysis, Ashley Kehr from the Real Estate Rookie podcast and Garrett Brown from BiggerStays join us to crunch the numbers. You’re probably thinking, “Short-term rentals always make more than long-term rentals!” but that isn’t exactly the case. With the added expense of short-term rental management, some deals may work MUCH better as a long or medium-term rental.

We’ve even got some bonus strategies to share to boost your rental property profits, like renting-by-the-room to get even more revenue and subdividing your lot so you can sell it and pay off your rental faster (more cash flow!). These deals still work in 2025, and today, we’re sharing exactly where we found them.

In This Episode We Cover

How to analyze a rental property as a short, medium, and long-term rental

The one overlooked cost you should ALWAYS account for on a short-term rental

A sneaky tactic to get extra cash if you’re on a BIG lot

Using the “coliving” (rent-by-the-room) strategy to get even more rent every month

Why short-term rental regulations are a good thing for investors

And So Much More!

Check out more resources from this show on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠BiggerPockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.biggerpockets.com/blog/real-estate-1126

Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠advertise@biggerpockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.

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