three possibilites I'm aware of
1. My h37 cutter has a stuffing box that is just a bronze top and bottom, the top bolts to the bottom with 3 bolts. Between is a big o ring that is squished bewteen them and against the rudder shaft. There isn't an adjustment. You can't really see it under the quadrent. This might be leaking, but is far above the water line.2. This stuffing box is attached to a fiberglass tube with a short piece of hose and two hose clamps. It could be loose, letting water in there. It is about at the water line.3. That tube is glassed to the hull and makes the bottom rudder bearing. It's not real substantial and mine was ozing water through the glass.With mirrors and lights you might just be able to see what is going on.There is one more possibility, but it is not the ruddershaft. The screws that hold on the flappers on the sides of the rudder might be rusted away or leaking. You should be able to see those pretty easily with a light.Oh, for sure get it surveyed, but don't trust the surveyer 100%. Make him show you or look for yourself.