Aloha and welcome aboard!
Good to have you here and asking questions. I left the SD area in the 70s and don't know what's going on there now. Had a home six miles from the border in Chula Vista. The marina wasn't there yet.
The SD area is nice and I've visited FL and lived near Pensacola
. Totally different. FL is very, very warm and humid in the summer. The land is flat. I suspect that boaters are accepted more in FL because there are many more places for boaters to go with sheltered water
and it is more or less a historic way of life. The proposition of hurricanes doesn't make it too welcoming though.
Good luck in whatever choice you make.