More thoughts
The factory mainsheet setup was the double pully on the stern end of the boom, with the sheet tied on the port side, then traveling from the port side over the top pully, down to a pully on the starboard side, back over the lower pully at the end of the boom, and to a clam cleat back on the starboard side. It works but you have very little control over the downforce on the boom except when it is virtually centered on the hull. A proper traveler along the transome, above the tiller, would be a great addition to the boat.As far as the rudder is concerned, the only solution I have ever been able to make work is to put the two bolts through the rudder so you are not depending upon the rope to do anything. If you have the holes in the rudder that are egged out, drill them out until they are round and to a recognized size, then go and get a HARDWOOD dowl from the lumber yard that is that size, coat it in some epoxy resin, drive it into the hole and then coat the ends with the epoxy as well. When it has dried, put the rudder in place and redrill the holes. Do not buy a soft pine dowl as you will end up just redrilling the hole and starting over. It has to be a hardwood. (Years ago I used oak dowls and the holes are still holding up) the other good thing is that you can repeat the process from time to time if you find that you have used the rudder as a portable depth sounder. Good luck.