Just a stone's throw away in Cape Coral you have the "Seven Islands" coming to completion. 

I'm best in the South Island. 

My mother and I have been renting a home on Long Island for the past decade.

The lady that bought them down was trying to buy an Island in Clear Lake CA that I had worked on with another developer in the late 70s and it could not be built on at all period.. she had this big dream would never have happened but Remington stole her 10k and she went on the war path..

Any realtor know seasonal rental market in Madeira Beach, Treasure Island and St Pete Beach?

I used expeditors for specific projects in NYC, but in Long Island, I hired an architect who's also an expeditor, where I bough a SFH, the previous owner done unpermitted work.

Padre Island.

I have two beachfront condos in Marco Island.  

I have currently 9 completed waterfront homes furnished and ready for Airbnb on Ft myers beach estero Island. 

And just an fyi -  you are not required to have on-island management.