You won't want 'leathers' for the TAT or any other mostly-dirt ride.
Relatively speaking, tools can be bought cheaply.
I suggest ordering all the junk you'll want before you arrive and having it sent to 'x' location.
Figure a day to outfit the bike with any aftermarket parts - OK, 2 days.
The only inexpensive motels you'll find in Florida will be in the northern part of the state, away from where tourists empty their wallets. Unless you're there for watersports, herding spoiled and snotty-nosed kids thru Disney Dollars, or visiting your grandmother, Florida basically bites the wad.
I also suggest buying your moto before you arrive, or at least arranging for the purchase beforehand. Communicating via email to the sales managers at several dealerships you find online should work OK and save you some money. They can also help you regarding insurance, or point your towards a few possibilities.
Make a list of everything you need. Camping gear can also be found easily and cheaply. Wal*Marts abound here. Adventure Rider Motorcycle Forum
is a good US-based moto site with many members and you will get lots of help there.
If your budget and time allows, I'd say fly from Cuba/MIA to Knoxville, TN and get set from there.