Re: 1959 Glasspar Trident
That's a good test for transom flex. Essentially, it shouldn't move at all when you try it. Also, take a rubber mallet and whack the transom, especially around the sides and near the bottom. It should make a nice solid sound. A dull hollow thud is a bad sign. You'll hear the difference in different areas, if there is any.
Take a close look at the transom eyes or handles on the rear of the boat, inside and out. They shouldn't move at all, and the nuts on the inside should not be pulled in, bending the fiberglass. That's an indication of rot higher up on the transom.
Frankly, unless you take a lot of pleasure in tearing a boat apart and doing months of work, if there's anything questionable about the transom, pass on the boat. It's very hard work, and very expensive to fix.
Same thing with the floor of the boat. Unlike the more expensive Avalon, which is a double hull design, I believe the Trident has a wood floor. Walk around every part of the floor. If you find soft spots, then the same thing applies as with a bad transom. Lots of work and money.
Don't be scared, though. There's a good chance that the boat is sound. Glasspar made good boats.
If this isn't the one, though, keep looking. There are lots of boats out there, and older ones aren't that expensive. If this isn't great, find another one.