UNLESS you have a boating background, don't do the live aboard.. Not until you've been a non livaboard owner..
Learn to sail dingys (Basics) it's alot like flying but on a vertical plane. Then mybe a J-24 to learn Kites. Then maybe someting you can take in the Inter-Coastal.
Not to dribble in your Cheerios...like I said, guys have made it work in the past, but if you're interested, I'd start learning about boats now to get familiar with them so it's not an "all-in" endeavor when you arrive to start the FRS. Oh, and also, don't forget you might get Lemoore or OKC as a duty station. Then boat owning adds a whole other layer of complexity.
So essentially, what you guys are all saying is that I really should be taking....baby steps?
But yeah, you guys are right, this was all a lot to take in, I should start working my way up to it instead of just trying to jump right in. Maybe start small, if I have some free time when I get to Pensacola and wait for API to start, etc.