I suspect those guys grew to fast and it got out of control..

For example, many of the nicer ski towns around Colorado require first month, last month, plus the security deposit upon move-in which can easily amount to $7k+.

With a natural in and use owner occupied housing, you could likely end up with 1-2 houses a year (each in a new city).The other option is when your baseball career is over, you will most likely end up back in your home town, so you could start the brrrr process there with maybe your parents checking in on the work the contractors and property managers are doing.Best of luck.

For example we had a group coming to stay for a wedding but after booking realized that it was almost 40 miles downlake from town.

That's why I posted, to provide people with real advice based on my experiences so they can avoid making the same mistakes.Providing greater buffer space for capital expenditures and controls is a good risk management strategy.

Small towns may rely too much on a single business or market segment.

True, Republicans in 2025 will control the White House and both chambers of Congress.You can easily Google how the legislative process works or just trust my Cliff Note: having a simple majority usually does NOT assure that Congress passes any bill, including tax bills.

Based on a gut check (checking the town population + location on google maps), this may be the case. 

Been looking around North Conway its one of my other favorite spots to visit each year cozy little town with a lot of local amenities.

Many times they do not realize the adding of the adu makes their existing unit rent controlled.