Yeah, unless you can assure him that you've done this before and are very confident in the way you present yourself, it would probably be best to just use a nickel. You can do as much or as little of the boat as you feel necessary, but I would absolutely check around the transom assembly and thru-hulls (especially underwater).
It's hard to completely relay this information via a forum, but the idea is to do a consistent tapping motion and listen to the sound. There will be "normal" sounds changes (varying thickness of resin/glass, supportive structures, all glass or plywood/balsa coring, etc) but what you're after (or actually, I should say what you don't want to hear) is the softer, hollow sounds of a wet core or the lighter/thinner sounds of delamination. However, you may find some small pockets of delamination, but this is most likely air voids and is not of great concern unless you find a lot. Given the age of the boat, though, most of these would likely have popped open by now. Blisters are another possibility, but it's not abnormal to see a few. The older resins used in gelcoats were more prone to this than the newer stuff. Chances are the boat is bottom painted and if it was done properly, that greatly lessens the chance of blisters.