I notice that, although they don't all agree, all those above have very good advice. We're sort of Missouri sailors. My wife's family is from Shelbyville and mine from Springfield, but we've been living on the sailboat since 1972,- mostly in Florida. I would only add that it's far more realistic to expect to economically survive living aboard with a job secured in one location and staying at a home port with ocasional cruises. It's far less likely to be able to remain mobile and continually "pick up" work at new ports. You will have a better chance of adapting to life aboard if you don't start with fulltime cruising. Also, the best slip rates and availability will bein the SE from the Chesapeake to the Texas Coast, with the exception of the "resort" marinas.
'take care and joy, Aythya crew