Nick, I spent 20 yrs working in E. Tenn and 10 years sailing and living on a boat in Miami!
Miami/Dinner Key has a good mooring
field in Coconut Grove that you can live in and Coconut Grove Sailing Club www.CGSC.org
is a blue collar sailing club that is cheap
to join and where you can improve your sailing skill. CGSC has a mooring
field but live aboards are not allowed.
From Coconut Grove you can easily explore the Keys and the Bahamas
as your skills improve.
Coconut Grove is a lovely place to live but most importantly the standard in the local construction work force is marginal and a good skilled worker will not have a problem getting work especially as a private fix-it-all guy.
PM me and lets us communicate! I will certainly trade
carpentry on my boat for sailing lessons