I hear you about the island and not wanting to miss it.
Florida is a gigantic peninsula. Odds are high if you swim back in, you will make it to land along it's coastline, somewhere.
I don't know how far out this SS guy was when he ditched his gear. But one thing is very possible given that decision. His gear (especially lines) now have an excellent opportunity now to kill large numbers of sea critters. The lines can easily entangle large animals like turtles.
I have spent tens of years on the water in Florida. For a stage there it was my job. This doesn't mean I am "right", it means tons of things have gone wrong for me over the years. At one point we capsized a research boat and several of us spent the night in the water around the Ten Thousand Islands. This time of year, hypothermia isn't really going to get you (I was cold... don't get me wrong). We all made it through the night, no worries and were found.
I have 100% confidence in our CG units here. They didn't charge us to bring us in.
The Stoli story was tragic. The water was much, much colder in his situation. I have to assume hypothermia set in with him very rapidly before the Rescue teams could find him.
I agree every situation is different. And the fact is, it's your life when/if this happens. It's your choice what to do.
I thought we were discussing this situation, in Fl., in the summer, 3 hours sun left - etc.
I will always stay with my gear given the Florida environment in which I ride.
If I were somewhere with zero rescue support and it was an island, with 40 degree water, etc., the thought process would be different. I think that's obvious.
One thing that we can take out of this for sure, many of us should probably be wearing flotation if riding in the Gulf/Ocean and out far enough from shore. I haven't been doing this and need to this coming season. Last season I had my CL fail and it took me over an hour to swim in (35 knot, side shore wind) with my kite. I was less than a 1/4 mile out. I was surprised how long it took.
Needless to say, I was very tired when I got in.