First, about the best way to ANCHOR a Hobie 16. I carried a collapsable small boat anchor in a padded bag in the hulls of my Hobie. You could also lash on to the tramplacing just aft of the mast. Make sure you get one that will work in the type of bottom that you will be anchoring to. Talk to you local marina about that. I tied the bitter end of the anchor line to the dolphin striker and front cross beam junction. The front crossbeam took the load.

Tinkerton. The reason the Hobies take on water when moored and other boats do not is that the Hobies (and other beach cats and day sailers) do not have a barrier coat to protect teh fiber glass from the water. Gel coat is not water proof. It is very porus and allows water to seep through over time. The fiberglass underneath the gelcoat is like a sponge soaking up all the water that seeped through. This will cause delam, blistering, and will fill the hulls with water.

The second part of this is the rigging gets beat up, as you noted. Other sailboats that don't have a rotating mast have tighter rigging. The loose rigging allows the mast to slam around since it can move some independantly of the boat. This dynamic loading (the slamming) causes higher laods than normal to be imparted to the rigging and anchor points. It's like jumping off a step versus slowly stepping down. you feel more of a jolt when you jump due to momentum. On the boats with tight rigging the mast and the boat are rigid so there is reduced, if not eliminated, dynamic loading.