You must be clear in your goals and path, and your JVs (as you so wisely call them :-) must know them as well....otherwise whatever the project is, it is destined for, if not failure, at least a tough path to the end...This may be (or is probably) the reason most investors fail at arbitrage, while those like you do succeed... 

Okaloosa Island, which is technically Fort Walton Beach just West of Destin, also has some room still for solid cashflow and growth over the next 10 years.

Do not limit yourself to "vacation" destinations:   Some of the best ROIs I have seen are in very "un-vacation" areas. 

Have you looked into the Emerald Coast (between Panama City Beach, Destin, and Pensacola)? 

I have grown up in the Warner Robins, Georgia area most of my life, but I have recently moved to Destin, Florida area for work.

From Panama City over to Pensacola (with a few superior areas such as Destin, Miramar Beach, Navarre, and Panama City Beach) is where I would browse.  

If you're really want a property along the emerald coast in the price range of $300k, look at the Gulf Shores condo complex in Destin or other complexes that are similar.

See choices as a first step to build on, not a final destination.

I have friends in other markets in FL that are doing very well with Airbnb that are not near any major tourist destination.

Good morning,I am in contract to purchase a STR in Destin, Fl.