Originally Posted by SlowButSteady
First of all, welcome to the asylum! Of course you're crazy...we all are! And probably 99% of us wouldn't have it any other way.
Now, here's my $0.02. I always tell anyone who is learning to sail, and has the itch to buy a boat, to get a sailing dinghy. I learned to sail on FJs and Lasers, bit there are dozens of models from which to choose. For $500 to $1000 bucks (maybe less, if you look around a bit) you can score a good used FJ, Lido, 470, et cetera, with a trailer and all the stuff you need to get out on the water. My preference would be a sloop-rigged dinghy, but a cat-rigged boat such as an Optimist, Sabot, or El Toro is almost as good for learning to sail. Then, when you have the boat, sail the Bejeezus out of it. That will be easy, because it will be small enough to haul to any suitable body of water, and cheap to fix all the little do-dads you're likely to break as you sail the Bejeezus out of it. You'll learn more (much, much more) about sailing by sailing the Bejeezus out of a dinghy for a season or two than you're likely to learn sailing a 20-something-foot boat every once in a while for years (which, sadly, is what almost always happens...regardless of intentions). AND, when you're ready to get a "real boat" (even though you actually have been sailing the Bejeezus out of a real boat), you'll have a much better idea of what to look for before you invest in a really big "hole in the water", into which you are going to start throwing serious cash (and, with boats, the cash is always more serious than you can ever anticipate; trust me on this).
OK, now, go out an buy that little 20-something-foot "yacht" --- no one ever takes my dinghy advice. Why should you be the first?