Re: Young liveaboard after Navy
I can't speak to the Navy side of your plan, But as far as the liveaboard on 30-35ft sailboat and being young, I'll say you have to be incredibly disciplined with your money throughout the process of saving. Don't try to reach a benchmark of $20,000 and be done saving, because the boat will become your home and you'll have to dump more money into it to make it comfortable and functional. I paid $15,000 cash, but it took about 7 years since I was 19 and came up with the idea to do it. I worked through college, though, not Navy, and it took a full-time desk job, a service (valet parking) job (nights and weekends, 50 hrs a week) for 4 years until I had the money set aside. Just enough, too. And now my credit card is racked up with the immediate repairs and details I've put into my boat.
It's possible, but just realize it's not a fairytale. It's fun and enjoyable, but because it's "different" people make it difficult to do. As in, finding a boat, finding a slip, etc. Having a Navy background by then will surely work in your favor, it's admirable and people of all generations respect it, they want to give back a little and will probably help you through the hoops more than the average person. Also, you'll go into it with more marine and naval knowledge which wouldn't hurt.
See how long you go with the dream in your head, if it fades in a month then forget it because it takes more than that to commit to saving and saving and saving for an unknown payout. But if you're like me and other people that do it, the dream won't ever fade, and you'll never second guess what your put all your effort into.
Good luck. And think about getting a job afterwards, it's more realistic because you will have to work to sustain living on a boat.
1985 Catalina 30 Std Rig "A Cenoura"