I would love to maximize cash flow but also do not want to be left on an island if there is damage. 

I worked exclusively in STVR property management on the island and currently work in long-term property management servicing the West Metro (Minneapolis).

I recently sold one I had on Seabrook Island because the club/regime/HOA were frequently changing the rules and making it harder to operate smoothly.

For instance, the area closest to Disney is actually less saturated and has many homes that can be renovated to a high standard and will book well.A bit further from Disney, in newer communities such as Solara, Windsor at Westside, Windsor Island and others, you can find deals in this market.

Not at all looking to stay strictly in the NYC area; have been looking around at markets in Long Island, Upstate New York, New Jersey, and the surrounding region.

I loved it.

Hi Rory, I'd love to connect with you.

I'm Fitz from Long Island, New York.

The Greater Phx area also has more places to expand, but be cautious of "island" developments that are separated from bigger cities. 

I do have a resource on island who can assist you.