I think you have received some good advice here about crewing first before jumping into a boat of your own. Here are some of my thoughts and why I might do it a little different now.
Here is a little bit about how I got involved with sailing. I have been trying to get involved in sailing for two years now, and just now am getting ready to actually, quite possibly sail my own boat.
First I had owned two power boats when I was younger and grew up not far from the shores of the Chesapeake Bay, so my experience on the water generally gave me a little head start. However, not as much as you would think since sailing is a whole different animal than pushing the throttle down and steering a course from point A to point B.
I always wanted to sail versus the "stinkpots" I had owned. I always loved how graceful and serene the sailboats seemed on the bay and wanted to experience that as well.
Good friends are hard to beat. One day about two years ago I was invited for a sail on a friends boat and that's all it took to get me hooked. From there I just went out on his boat as many times as he needed an extra hand. At first I had no clue what I was doing except doing what I was told by the Skipper. (a patient man) He still tells me what to do, but different things now than in the beginning. He still gives me crap about my knots too.
Sailing Clubs and Associations
Anyhow - That same Skipper introduced me to a local sailing club in Annapolis not far from where I live and they provide sailing classes for a variety of levels of seamanship. I think clubs are one of the greatest ways to meet people and learn more about sailing faster than going it alone.
More Crew Needed than Humanly Available
The club also has at its disposal, a 44 foot sailing yacht for club operations and classes which always needs crew. Through this organization I have met many other sailboat owners that need crew. Also through the local marine store I have met people involved in racing that always need crew. The local Sailing News Magazines "Spinsheet"
has a section just for people looking for crew and people looking to crew. I think if you wanted you could find a boat to crew each week and gain all kinds of good experience.
So my point here is that, more than I originally thought, there is a higher need for crew than one would think. I have more sailing opportunities now than I ever did before. I don't have the time to take these good people up on their sailing opportunities.
Last year I started looking around for an inexpensive sailboat because I thought it would be great to have my own boat and the freedom of being able to take it out when I wanted and on my terms. I was lucky and had been pointed to a little C&C25 that had been taken care of over the years, but not without its own share of issues. As I get this boat closer to readiness I see the wisdom in sailing other people's boats.
So before running out to buy a sailboat, I would suggest getting more deck time on other people's boats. I'm glad I bought my boat, but looking back I could have really done without it at this point in my sailing experiences. It is providing my a new learning experience but a lot of those lessons have not been on the water.