I can still remember my first day in an El Toro. By the afternoon I wanted to race
everyone around the pond. I was 16 and hooked. Being young and foolish, the idea of being farther out on the sea didn't phase me at all. To answer your question: It depends on the kind of learner you are. Some do very well with books
, some don't.
Plenty of good replies here.
There are two things here though. Will you love sailing and will you love being on the sea for a week or two at a stretch?
Learn on a FUN small boat. We often mention Lasers because they are fun and easy and the response to actions, the education, is immediate. Now many people learn to sail and love it and don't take it farther than that.
Some want to cross oceans, buy a big boat and go. I know of someone who did that. He got out a ways, got sea-sick and decided it wasn't for him. He came back and sold the boat... at a loss, pretty big one I heard. A friend of mine bought a little boat, packed it up for Hawaii
and asked me to go. 2 days later he was still so sick he decided it really wasn't for him. We came home. He continued to live aboard for years though.
Once you discover you love sailing and look forward to any chance to get back out there, then start bugging people to let you crew on bigger boats, racing
on Wet Wednesdays, and some coastal hops, afternoon jaunts, ask lots of annoying questions and let the thing, the passion, grow organically on its own, at your pace, in your way, before you make the leap to bigger boat ownership
. Take the classes
too so you can charter
bigger boats as you progress. IMO.