I chose the opposite tack to what Drynoc proposes. After learning to sail, I took six years to learn how to sail well - mostly by racing with some of the best people I could find. Then I thought long and hard about what kind of sailing I was likely to do. In my case, I realized it would be mostly daysailing with the promise of the occasional weekend cruise, at least as long as I'm still working.
I also recognized that my most frequent crew would be my wife, who really doesn't like sailing as much as lounging on the boat, so I'd essentially be single-handing. I learned from sailing on friends' boats with my wife that a large cockpit was essential to her well-being, so I decided it would have to have wheel-steering even though I'm partial to a tiller. Finally, I'm not real handy, so it would have to be in pretty good shape to start out - I can handle routine upkeep - so I was prepared to spend more.
The upshot is, I bought my first boat 6 1/2 years ago, my wife and I both love it enough that we resisted the temptation to sell during a financial rough patch, and I expect it will be my last boat, barring unforeseen disaster.