I started sailing long before my 20's in sailing dinks, but by my 20's had a 25 foot Catalina
, then 32. Had kids
and had my first on board at 5 days old, and we have not stopped from there. I am currently 35.
You can do it, just don't follow the American Way. Live under your means. Don't buy a house (they are nothing but expensive). Live in a cheap
apartment and work your butt off. That is what I did, and the wife.
If you want to learn a lot about boats, move about an hour north to Lake Texoma. That is where they build Valiant's, one of the best ocean crossing
boats in the world (believe it or not). Cedar Mills Marina & Resort. They are VERY nice and as long as you don't look like a modern rock star, might let you walk the docks and look at some awesome sailboats. I have no idea if they are hiring, but it is worth asking. Pay is low, but knowledge is high. Valiant yachts: (903) 523-4222. Good luck. PM me if you have any questions. I will help if I can.
PS The advice on being crew is good too. PM me for that too if you need help there.