Re: Young liveaboard after Navy
Your plan is entirely possible. It would take a tremendous amount of discipline on your part to save the money then move on after 4 or 6 yrs of service. As far as i know there is no "unemployment plan" after service (other than unemployment payments for 6 months), for any branch. (I was a recruiter for 6 1/2 years) If you complete at least 3 years of service you qualify for the Post 911 GI bill (google). Which does pay a small monthly stipend (E-5 Basic Allowance for Housing, single rate) WHILE you are attending college. (That's 9 months a year) I doubt you could pay marina fees and live aboard and go to college full time and work a job. It's possible though.
Do 4 yrs, get the Post 911 GI Bill, go to college and start a great career or... maybe do 20 years in the service, travel, see the world, buy a nice sailboat and get it outfitted. Then when you retire you can travel the world with a pension coming in.
At one point i was just like you; i was going to do 6 years in the service and move on with my life. Yet, 24 yrs later i'm still in. I'm on the second phase of my life. When i retire in about 6 years the boat will be ready, the kids will be out of the house and the wife and i can sail off into the sunset. Whatever route you take you must plan, be responsible, make contacts and friends and enjoy life as it comes along. I have no regrets for the sacrifices and freedoms that i gave up early in my career. Now that i am at the sunset of my career i am having more fun than ever. (and more time to sail).
Joining the military is a commitment not to be taken lightly. Once you have taken your oath you are giving your life over to the military. Please pick a Rate/AFSC/MOS (Jobs) that is highly portable to the outside world, it will help you tremendously. There is not a high need for infantry, but, If you become a registered nurse you can work anywhere you want and make decent money.
You don't need to be in the military to buy a boat. A friend of mine bought a Catalina 30 for 3k and outfitted it as he needed to. If you work hard you can do the same.
Do your research, talk to people.
Best of luck, i'm sure you will get lots of input from everyone on sailnet!! Cheers