I'm born & raised in Sarasota, still have family there. HOT, HUMID weather and beautiful beaches obviously. You never know about hurricanes but the way the city sits it's not as likely as say Miami. Lots of wealthy people so a business that caters to them is good. My little brother has a pool cleaning business that does okay. Houses are pretty affordable, he bought a 3 br 1950's concrete block home in foreclosure for $219k. With all the old people, medical care is excellent. Manatee county just to the north is a little less pretentious. All the ugly highrise condos kind of spoiled Sarasota for me, as I remember what it was like before, but that's "progress." Take your time looking around...maybe rent a place first. There are still pockets of 'old Florida' charm to be found between the cookie-cutter developments.
A lot of people move to Florida thinking expecting to find the promised land and they are disappointed. Oh and I forgot to mention the bugs and mosquitos, I grew up with them but they freak some people out.