I agree with Matt, if you have sailed something before, sailing is the same basic concept no matter what the platform. My wife and I never really even sailed before we decided to get into Hobie sailing. So, we went to the keys and got a 1 hour lesson on a getaway, then rented it for another hour and the rest is history. A couple of months later I was coming home with my "new to me" own used 1995 Hobie 16. This was only about 3 years ago.
(Should have seen the look on her face when I told her the H16 did not come with bench seats to sit on, then what her face looked like when I told her she had to get her butt in a bucket and hang off the side

)
As for what to look for in a used boat, I strongly suggest coming by the club on a saturday we are their setting up to race, as we can easily show you what to look for in used boats, as there are a number of boats on the grounds that we can point to and use as examples of what to look for and what to avoid.
Hope to see you on the 15th!!