Go for it! I started living aboard (though not cruising) in Oct and I'm loving it. I discovered that I couldn't get insurance for a boat larger than about 37', however, due to lack of experience. The only experience I had was an 8-day (living aboard for the duration) ASA class. You should definitely take such a class, both to learn how to sail and to get some experience at living on a boat (whether or not you can deal with the constant motion, etc). I hope you'll find an insurer willing to cover you, or a smaller boat that fits your needs (there are some really great layouts that make smaller boats feel larger, but they tend to cost more).
1979 Gulfstar 37 Laissez Faire