I don't know where in life you are, but just do it. I'm sure other members's will roll their eyes (as in "here he goes again") but I'll give you a synopsis of our history. Nov 2008, my son and I decided to take up sailing as a father-son thing. Told Mom a month later (after my spine filled in!) She loved the idea. A month later, we plunked down $2200 on a Lancer 25 knowing nothing about sailing. And I mean NOTHING. Turns out, she is the perfect boat for us. Quite a blessing. We spend most weekends on her and it isn't that expensive. The trick is, she's a trailerable. We launch every time. It takes about half an hour to raise (step) the mast and launch her. Worth every minute. And by towing her, there are no slip or storage fees, just an extra $5 in gas, depending on the trip. So, don't worry to much about the big costs if you're willing to trailer. And in case you're wondering, I had never towed anything before either. When it comes time to buy, try to wait until the fall. Just like motorcycles, prices fall then.
So, just do it!