Originally Posted by BarryL
You can buy a decent Catalina 22 for $2-3K. Sail it for a year or two, have some fun, learn a lot, then dump it for what you paid for it.
What this really means is you can buy a Catalina 22 for $2-3K, dump a lot more money into it over 1-2 years, sell it for a portion of what you put into it, and have had the opportunity to sail your own boat and learn a lot about fixing up and maintaining a boat that you do not intend to keep.
Although the Club idea is nice (did that for a year), there is no substitute for owning your own boat and learning to love the care, maintenance, and improvements you can make along the way, even on your first "junker" boat. If you have the means and a little time, I would encourage you to buy the cheap (but "sailable") boat, learn on it for a year or two, learn what feature you like and don't like about it, then buy the "keeper" for some serious sailing that fits your dreams. Along the way, it has been helpful for me to crew on a local racing boat, and spend countless hours (I think my wife is actually counting....) at the local West Marine/online stores searching for the perfect solution to a nagging problem. Owning your own sailboat is 1/2 sailing/seamanship, and 2/3 maintenance/care/upkeep, much of which we actually like doing and find incredibly rewarding and relaxing. Don't forget the expenses, though.
Good luck, and get out there....