Will,
The H-16 is a great boat. I have owned mine for 21 years and have been completely satisfied. I should think there would be a lot of boats available in Florida but I don't know how they stand up to the UV in that strong FL sun. Buy the best boat you can afford because you want to sail not work on it. Further north I can see that demand drops in the fall but I wouldn't think that to be true in FL. Here in NC, spring and fall are the best sailing times. If you wait, you lose that time you could have been sailing.
I wore the bottom of the hulls out from dragging it on the beach. Someone poured two strips of resin on the bottom of each hull for me and I haven't had a problem with it since. There used to be a kit with metal (copper?) strips that you could buy to repair and reinforce the bottoms.
Howard