Re: "Free boat" seaworthiness
Most respectfully (I mean that!) if $350 is going to slow you down, I think you should definitely not buy the boat. It's just the beginning of a long road. I bought a pretty good boat this summer for $6500. I'm probably going to put $6500 into it this year to fix a lot of things I discovered along the way (this is after having it surveyed). Money just goes. I'm currently spending money I don't have on things I need, but I have a good job and can pay the stuff off. It's a long story.
Seriously though, there are awesome trailerable sailboats and you can have an amazing time on them. I don't regret going with the boat that I ended up with, but an Oday 2+2 or something like that would be cheap and you could do plenty of amazing stuff with it. You'll be learning on a real boat instead of putting money you don't have into something that ultimately isn't worth it. And if you can't afford hauling and launching and dockspace etc...you can't afford it. It's going to not be fun.