We bought a Lancer 25 November of 2008 with no sailing experience, no trailer, no tow truck. Everything WAS thought out before we signed the check. I won't bore you (or anybody else who stumbles by!) with all the details, but the first time I ever sailed was the first time I hanked on my own jib a 1/4 mile out of Saco, Maine. We are talking CLUELESS! (but careful) We've sailed around 750 nm in two years of weekends in all kinds of conditions and absolutely love it. We trailer every time so we're pretty good at stepping the mast and getting her ready. A few things to keep an eye out for when buying:
1) draft: a long keel makes her harder to launch off a taller trailer
2) head: smaller boats = smaller heads, or maybe in the middle of the cabin!
3) trailer brakes: make sure they're there. Mine weren't. $350 kit to replace
4) tow truck: make sure it can handle you're baby.
5) head room: some boats are "pop top", fine for anchoring but not moving
6) roller furler: very nice to have for a newbie
7) Outboard: make sure she runs well.
8) standing rigging: check all ends for corrosion or fraying.
9) Find a review on your boat to see her handling
10) are you handy or loaded? Sailboats require one or the other, sometimes both.
Do you know how to make as small fortune? Start with a large fortune and buy a sailboat!
Well, welcome the family and good luck with your search.