If you are not going to live in it an FHA refinance is probably off the table.

I don't want to leave a lot of money on the table, but I also don't want to still be holding this when Winter rolls around.

However since I built the relationship, he allowed me on the property to fix chipped/peeling paint and waited until OCTOBER, which was when I finally got to the closing table.

Andrew, honestly just keep going.You'll be worth 8 figures soon.Not many people love their jobs, but it puts food on the table and you are clearly good at it if you've been doing it so long.Use some extra income to start getting into RE investing.If you get a seller to carry 15% in 2nd position, you just need a 10% down payment.Its tough to do but everything in life takes sacrifice.

This may or may not be helpful, but for the sake of throwing all the info on the table to keep this guy in jail, I thought I would chime back in. 

Only caveat I would add is that the OP mentioned that they no longer live in the property which takes owner occupied options like FHA 203(k) off the table. 

To be successful right now in STR, you either need to go all out and beat everyone else on their table stakes (pickleball, basketball, game rooms, saunas, hot tubs, etc.) or you need to understand the market better than anyone and pick a niche for that market.Right now, you are one post in and just asking for someone to tell you anywhere in the United States to invest, which is silly.

There is no better way to learn than watching real world first hand.The rich teach their children about money through first hand experience and at the dinner table.

@Jonathan Feliciano Ask yourself what competitive edge does this boots on the ground partner brings to the table a reputable GC and PM can’t provide?

While this may converge with a planning commission meeting for 2024 budgeting, if it is at least on the table for 2025, that would be exciting.