Wow! I guess it's a good thing that I moved to Ft Myers before I read these responses to your questions. I've been here for not quite 2 years, having moved from San Francisco
for full time warm water
sailing. As for sailing, you know what west coast
Florida is like as far as winds and weather
are concerned. Great area for gunkholing from Charlotte Harbor
through Sanibel and Captiva south to Marco Island which is at the head
of the 10,000 islands. I've pulled into places there from Panther Key south to Little Shark River. Bugs aside, these are easy sails
from Ft Myers. When with groups, we stop in Naples, then Marco, then into the 10,000 islands with opportunities to stay in Goodland and Everglades City which are still like what they call the old Florida. I found a great sailing club, the Caloosahatche Marching and Chowder Society, that has friendly cruising, racing
and socializing. Weekend sails
to "Danger Island" (actually Picnic Island at the southern end of Sanibel) for picnics, dinghy racing
(speed + style points). As for places to keep your boat, like any place in Florida, you have to look and get local knowledge. I started out at Tarpon Point Marina in Cape Coral
, ~$10/foot plus electricity- for my 43 footer I was spending about $500/month. Had to go through the Sanibel Causeway bridge, took about one hour to get to the gulf. But after looking around, I found a private slip in Fort Myers
Beach that is $250/month and is 25 minutes to the Gulf. Two big non-baoating factors; housing costs and schools. I don't know what it costs for a house in Clearwater but everything in SW Florida went up big time. Your new/candidate employer can probably give you a sense of that cost. Schools are the big variable, they range from very good to unbelieviably awful.
In summary, the sailing can be really good. I've used Olsen marine for major repairs
, given that they are the only boatyard that can haul a boat south of Port Charlotte, they charge for there services, which are uniformly excellent. Don't worry about the sailing, do your due diligence on housing and schools.