I toured the Atlantic Coast route in 2007 from Boston to Key West. The keys weren't bad, but certainly not the best area we rode during that tour. Wild/stealth camping and doing it on the cheap is going to be very difficult (you mentioned something about "living off the land"), but there are a ton of hotels, motels, and a few campgrounds along the keys. It won't be cheap, that's for sure. The weather should be pretty good, but plan on wind and maybe some rain, but it won't be cold rain.

Enjoy your tour and post a ride report when you're done!