I read a couple of books, bought a small, cheap boat and taught myself. I then crewed on bigger boats racing, read lot's more books and bought a big boat. Reading and hands on have always worked for me. Nice post by the OP BTW.
Sorta kinda for me. I sailed one day on a friends boat (Catalina 25) and was hooked. Sold both my motorcycles a couple months later and bought a 23' Aquarius. I'm in my second season. I still don't know what a lot of stuff is called and last season sailed with just the main. This year the jib goes up. It took a bit of getting used to on the heeling part but I ok with it now...sorta kinda
At least I feel comfortabel that my boat won't tip over, me fall into the water, get tangled up in the rigging and drown....sorta kinda.
Anyway, I'm having fun and that's what matters.