Hey Steve, welcome. I assume you are in the military or the oil industry - then going home to an area that you have contacts in Florida. You are on the right track with doing your leg work well ahead of time (posssibly even to far ahead - the industry can change alot in two years). You will get a great understanding from the good people on this board.
My humble suggestions:
Craw before you run: invest in the equipment you need to do a job correct but don't over invest - save the bells and whistles for later. I see this all the time on these boards, real nice equipment for sale with +/- 100hrs.
Educate yourself: ask questions and read all the message boards. Go to a PWNA or other trade organization convention. I think you have this covered.
Work for someone else: Theory to reality is a road to learning at the school of "hard knocks". I'm not saying you have to work years for another company to "pay your dues". Working with another contractor that you have networked with for a couple of days in your area of interest, this should do.
Buy another business: It sounds like you are "getting all your ducks in a row" and going to the Sunshine State with a bit of change in your pocket. why not look at buying an existing company with an owner willing to stay on (transition period), equipment and most important accounts. You could have the best Equipment, soaps and knowledge in the world, if you don't have work you will be selling your equipment and looking for work when the savings run out.
Focus on marketing: If you can't find a business to buy or that idea does not apeal to you - concentrate on marketing. The best resource for this would be our very on Ron Mussgraves. It is easy to get caught up learning the technical side and buying equipment - that is the fun stuff.
I don't know your specific market in Florida but a general stereotype of Florida is the season is year round (very good) and the customers are price sensative (very competative market on price). Any feed back from FL contractors on this to help steve?
I'm not triing to come off as a know it all or someone "who has made it" (I'm not) - just helping you in the right direction. Good luck!