AND try to find a market where you do not have to compete as much with 2nd home demand - a place where people go to vacation but is not top of mind for a rich guy's vacation home destination (ski town, lake house, etc.).If you are asking for the secret market that returns 20% cash on cash without any renovation or difficulty, that doesn't exist.

My girlfriend and I are interested in buying into the upper Michigan STR markets (Traverse City, Charlevoix, Petoskey, Bay Harbor, etc), hoping we can take advantage of the hot vacation rental market up there in the summers and the popular ski slopes for the winters. 

Typically, short term vacation rental management in our area of coastal Oregon can typically range from 20-35% of the gross revenue!?

A totally managed vacation rental - think ski condo in a central managed destination. 

The best find I ever had was a plastic kiddie pool with a built in slide in an old tool shed that was left behind so it definitely beats me.I know most people would advise reinvesting your findings or maybe splurging on something you've always wanted like a car, vacation, trip to space, or a pony.

We vacation there regularly:  Dauphin Island - 2017, Orange Beach - 2022, Gulf Shores - 2023, Fort Morgan - upcoming 2024.My guess is that Dauphin Island doesn't see the same appreciation as Gulf Shores, Orange Beach, and places eastward. 

Some of us are in vacation markets that only survive due to the visitors that frequent the area, and the STR that house all the guests.

Vacations are to relax and de-stress.

I'm sure you've seen this website, but this is the full info: https://www.savannahga.gov/1476/Short-Term-Vacation-RentalsYou could buy a property with a STVR certificate already in place.You could by on Wilmington and Whitmarsh Islands - they are not regulated yet.

Then purchase a vacation condo/cabin for trips and quality of life.