When I have shopped for watercraft, I have often found myself right in the middle of an emotional love affair with the process. Sometimes caution falls to the wind in favor of the excitement of the moment. When that occurs, I try and manage to put things into perspective;
Hire a surveyor, find a friend or who knows the boat I'm looking at, or at least read all of the possible problems that can occur to the model I'm looking into. For the Montgomery 15, I guess about the only major concern I would have is to be certain the centerboard operates properly. Most are stored on trailers and it's pretty easy to see the obvious problems of rare blistering and physical damage. And most of the other problems that plague other balsa cored, hand laid craft are thankfully not present in the Montgomery line (excellent design and craftsmanship abounds).