Thank you, everyone, for the helpful reviews! We've been doing some more research, and are almost sure we're looking at a Silhouette, so thank you mitiempo and killarney.
We currently plan to start on KY lake and perhaps Cumberland, emoney. The plan of the man is to build his confidence on the lakes quickly so that we may move out to coastal sailing. We'll also use the lakes in the months we're unable to travel with school and work.
Taking everyone's information into consideration, along with the fact that Michael would prefer something larger, we're focusing on an O'day 22' at the moment. We both seem to think this will suit our needs more adequately than the Silhouette, but we must keep it in mind for the price, for now.
Thanks again, everyone! We greatly appreciate the knowledge from seasoned boaters and look forward to becoming a part of this great community.