This is very much a driving destination and we get visitors from several different states because it is centrally located and most of them can be here in a half day drive.

Ambergris Caye was the top tourist destination on Trip Advisor in 2013 and 2014.  

This journey is as much about the process as it is about the destination.

But to touch on some of your points:-Costs to build are probably some of the highest in the nation, other than maybe Telluride or other vacation destinations. 

My STRs are just for fun and are true vacation destination rentals.

Downtown str's have done well and it's convenient to the front gate of NAS Pensacola but you could also consider near the beaches of Perdido Key since that is convenient to the back gate and it's a more traditional tourist destination. 

I was very bad at it so now am cruising with a bookkeeper for about $200/month.

It is also the top tourist destination in the US, and it is a year-round market with fairly consistent performance year after year.

It costs about $2000 in Destin, FL for instance to convert a regular residential use to STR use permit if it's the first time the house being coverted for usage.

The beach is always an attractive destination and Oregon is no exception.