We're not Loopers, but two quickie "advice" ideas anyway:
1) If you haven't already, check out the Loop association (AGLCA).
2) Get your boat at least 2 years before you intend to set out on that trip. Even earlier, if you won't be able to use it a lot during that period. That's your training time, where you get hands-on driving and maintaining experience.
FWIW, We've had this current boat for going on 12 seasons now. Handling hasn't been much of a learning curve in our case (especially given carry-over experience from previous boats)... but I'm still learning how to service/fix stuff.
South River, Chesapeake Bay