Most of us were in the same situation, and pulled the trigger on a boat.
Taking classes is a good idea (I've taken some), but in the end it isn't a substitute for getting out there on your own boat. The Catalina 27 is widely seen as almost the "perfect" small boat. It's big enough to be comfortable inside, but small enough to be single-handed easily. The C30 is the "big brother" to the 27, and is a very nice boat. She's bigger, with more creature comforts, that's for sure. In fact, the C30 was essentially what I was looking for in my most recent purchas. One be plus to Catalina is that there is a deep aftermarket for parts/accessories/etc.; you can find just about anything you want/need for them pretty easily. Anoter advantage is that there are excellent owners forums that focus on those specific models, and there are usually LOTS of participants. I like SailNet because I get great feedback from a lot of people about various questions/issues I may have, but some times (especially when it's your first boat) it's nice to hear from someone with the same kind of boat as you, and that's easy to find with the Catalinas. Catalinas also tend to hold their value a little better than other boat brands because they are well-known, and people know what they are getting when they buy them. They are kind of like a Toyota or Honda - certainly not a high-end vehicle (in the case of the car companies, both have luxury lines that have much "nicer" cars) - but good, reliable, and well suited for their intended purposes. I'd bet you can find both C27's and C30's in your area in your budget without much of a problem, and then you'll be able to get out and sail when you want, rather than being subject to the times when a boat is available as a rental.