Take something you understand (ie for most people it's cars) and find parallels that you consider important. Easy to fix yourself, cheap
to find parts
, easy to operate. Research
the boats out there, and go buy one. Make sure you like the boat, you feel good when you step on it or see it in pictures; otherwise you'll hate working on it and spending all your money
on it. When you go to buy it keep in mind it is a buyers market, no matter what the seller thinks, and if they don't want to sell move onto the next one.
Most importantly go while you can, life's to short to listen to what concerns others. If you want to jump on a boat and sail go for it, you won't regret putting your dreams into action even if you fail.
Plus people make boating
sound so complicated, it isn't and you can learn everything from books
and videos and friends. If you love the idea of hard work and freedom, get out there as soon as possible.
You won't learn what you are capable of, or learn as fast, or learn your own cruising style if you are always crewing
on others boats.
If you're motivated and willing to work hard, do it before life takes away the chance.
my 2 cents.