After living there for 4 years, I have a few thoughts.
The weather is pretty damn nice most of the time. Summers are extremely hot and humid (but you deal with it like you deal with cold and snow up north).
Snowbirds are a-holes (most), with a ridiculous sense of entitlement. But again, come March they go back home. Traffic is bad, but tolerable when they flood the area.
There is a giant lack of culture (unless you spend time in the hispanic communities).
The food is mediocre. If you love seafood (as I do) it takes some time (or a local) to find the really great places. Avoid the touristy places (most), unless it's off season.
If you love the water, get yourself a boat (or make friends with a boat owner) ever a kayak. I miss paddling the back waters the most!
There is very little industry there aside from service and retail, so the economy is in the crapper most of the time and the housing market is in the top 3 worst in the country (at least Lee county is).
Florida state education was ranked 48 out of 50 in the country (at least it was two years ago.
Depending on your age, it can be difficult to meet decent people. There seems to be a gap between the ages of 25-40...I'm right in the middle, so unless your fresh out of college or close to retirement, there are not too many quality people to hang with.
If you like laid back, any tropical region will do. I do miss flip flops everyday!
I miss fresh fruit...bananas, oranges, grapefruit, limes and coconuts in my back yard!
I met some good people and will stay in touch, but compared to back home (Pittsburgh) not too many people I met know the meaning of true friendship down there. This is also true of Orlando area Another Florida city I lived in.
No don't get me wrong, I enjoyed most of my time there, just not the tourists, sweating at 5am before the sun is up, fire ants, and mosquitos (or no-see-ums)!
Will I go back? maybe, definitely to visit as my girlfriend was born and raised in Cape Coral.
If your looking for an excellent bike shop, I can recommend Naples Cyclery.
I had the extreme pleasure of working for them for a short time before moving back north. Great group of cyclists!
Food, Skip One seafood or 3 Fishermen both in Fort Myers.
Beach bar...The Cottage and S.O.B's
Bar/ restaurant...Blue Sushi, The Pub in Naples at Mercado, Landsdowne Street in Bonita.
Best authentic Mexican food...Taqueria San Julian, its a little A-frame building corner of Bonita Beach road and Old 41.
If you like wheelin', there are some swamps down Bonita Beach road on the left that have some decent (for SWFL) trails. don't go at night or in the summer unless your lifted tall with a snorkel and a group who knows the area. Recovery gear is a must and stay out of the restricted areas!