We did the Southern Half of the Loop in 2002-03 on our Grand Banks 42 Classic after being river rats on the Tennessee River for many years. We started by reading a lot of books and every Passage maker magazine printed as well as going to a dozen Trawlerfests. After volunteering to crew on a boat from NYC to Miami, we felt ready.
There is a lot of wisdom here and even more opinions. I think Ted's advice to get off the regular route and take side trips is a great one. You will be starting not too far from where we ended, at Lake Guntersville. Just remember to go counter clockwise, they do it that way for a lot of reasons. Some folks make it a two year endeavor so they can more fully take in the stops and the side trips. Good luck and Welcome to Trawler Forum.
One tip: Buy a boat from a Looper, not only are you getting a tried and true vessel, with many kinks worked out, but often you will get lots of cruise, anchorage and guide books that alone would cost big $$$, plus you get some first hand advice from someone that has just recently been there, done that, on that boat.= Priceless.