If you live 30 mins north of Tampa, you can drive backroads to WDW and get there in 1:40, w/o dealing with the I-4 deathtrap drive. Busch Gardens has a lot of events that cater to adults (Real Masters Music, Food & Wine and concerts, etc), and some of it is on school days, which makes BG a great place to meander around with friends on weekdays, even if you don't do the thrill rides. Approx two visits on an annual pass and you break even compared to purchasing individual day passes. Selby Gardens is another good find 1 hr south. If you have a Bank of America/Merrill Lynch debit or credit card, there's a list of
museums with free admission the first fill weekend of each month. St Pete is a fun visit, Dunedin is artsy (not been there yet), and if you go further north (Pasco, Hernando), it gets more rural.
We elected to buy in a gated community that has a pool, and happy that we don't have to maintain one ourselves (materials, insurance, etc). As a former new englander, I cherish when the weather gets below 70, and don't mind putting on jeans and a fleece, but that's a different perspective than true FL natives. Then again, we come north to CT for 2-3 months in the summer. We love the seafood down here, but also miss some of the northern varieties. We are former USAir/American flyers, so our only issue is that there's always 1 connection to make for most . Upside is TPA is getting some direct flights to Europe (Amsterdam, possibly London), so that's cool.
If you are into craft beers, there are a lot of small breweries popping up. The food scene in Tampa is quite diverse too. Feel free to PM me if you want more info as I could type forever about random things.