Thanks for the quick replies!

The license I was researching was for the larger sailboats. It was required to be able to rent larger boats. I don't think it's required unless your renting...

Renting is expensive as well, so I think $800 for a boat I can take out whenever I want, realizing theres going to be some maintenance costs, is better on my wallet in the long run.

Looking into a club on post is a great idea, however, in Chicago I wont be near anything.

This guy has had the boat for around 7 years he says. Says that the sails are in storage and the boat has been sitting outside storage for a while. He said that I might want to replace the tires on the trailer, and he said the tramp might need some patching.

It sounded like he hasn't seen the thing in a while. I'm going to go have a look see this weekend. I wont be terribly surprised if it isn't in the kind of shape he says its in. We'll see. I plan on taking plenty of pictures. Perhaps I can post them here and people could get a general idea of what kind of shape its in.

Basically, I would be buying this thing, strapping it to the Forrester, and driving to Chicago. If $800 is a really good deal for this cat and a trailer I'll jump on it. If not, I'll wait till I get to Chicago.

Concerning the trailer, what exactly is needed to make it road legal? Do they require plates? Registration? Is it a state by state thing? What about the boat? Should there be a title or something? Does it need to be registered in the state I sail it in?

As far as getting him to take me out I don't think it's going to happen. I was just given the green light to move by the Army so we will be moving in the next week or two. I've been trying to get this guy to take me out on his big 27 some odd foot sail boat but he is busy for the next few weeks.

Stinks that I have been here for a year and just now find out about his boats.