November 22nd, 2025

Good morning STR Report Community, and welcome to The STR Report’s Weekend Digest!

In today’s issue, you will find:

📱Weekend Digest: Real people. Real properties. Real wins.

📬 See our collection of newsletters here: Prior Newsletters

☕ Good morning, STR Report Community!
Welcome back to The STR Report’s Weekend Digest — your go-to scroll for real stories from real investors.

Here’s a story from another real investor and how investing in short-term rentals changed their life for the better.

Real people. Real properties. Real wins. ↓

I got started in real estate back in 2008 at 23, right in the middle of the housing bubble. I purchased a 2-bed, 2-bath condo and moved in. A few years later, my then-fiancé and I moved out, and I decided to try renting it out. I self-managed the property and kept it rented for 14 years, earning around $100/month at best. Eventually, I paid it off and used a 1031 exchange to roll the proceeds into a run-down 4-unit apartment building in the same city.

As tenants moved out, I renovated each unit, which significantly increased the property’s value. I sold it in 2023 and completed another 1031 exchange—this time into my first Airbnb. I was one of the early adopters of BnB Turnkey, who helped me identify a market that matched my goals. They handled the launch and continue to manage the property through Home Team.

In 2024, I acquired my second Airbnb—a 6-bedroom super property on 5+ acres. I partnered with an investor, which allowed us to add premium amenities like a pickleball court, etc, that I wouldn’t have been able to fund on my own. Initially, my partner chose the property manager, but they didn’t work out. We quickly switched to Home Team, given the success I was already seeing with them.

Most recently, we closed on property #3, using private money for the first time. We plan to launch it before the end of 2025 to take advantage of tax benefits like bonus depreciation. Our goal is to add at least one more property in 2026.

-Brian

See Brian’s properties below:

Waterfront with Heated Pool, PuttPutt, Fire Pit

Sleeps 14! Pool Hot Tub Sauna Pickleball Arcade

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