He bought a home for himself in Lodi California but work in the Bay Area long story short he can’t deal with the commute anymore and decide to stay with a buddy close to work.

That's right and wrong.There's a housing short, where it counts.

In short, the current PM ended up not having a valid broker's license to be operating as a property manager in the first place, so that's on me for not verifying ahead of time. 

An easier route would be to convince him to go in on the short term rental together in a partnership. 

Hello everyone,I’m a Canadian looking to buy a short term rental vacation home in the Kissimmee area.Currently we own a long term rental home in Winter Garden which we bought some time ago, and will be paid off completely in Feb 2029.  

In short - if you aren't licensed to do the work -  your services aren't going to satisfy the permitting agency.  

That's why many businesses just close instead of being sold.Real estate investing provides a lot more creative angles than the stock market, but on a conceptual level, nobody would seriously attempt to replace their W2 income in a few years by investing a few thousand dollars in the stock market.

What @Anna Sagatelova said about Cleveland properties is also true in Akron. 90% of the housing stock in the city of Akron was built before 1970 and there are quite a number of really fine A++ older homes especially in west Akron.

You're going to have to scrap like crazy to break even - think rent by the room, short term, mid term strategies that require more work.

Hi Jack, there's a lot of old stock - I've traveled there and seen it myself, but word is out of Syracuse and it has shown up in various BP "lists" over the past 12 months as well.