'Bearing' mounting
The 28.5 has two doughnut like nylon like bearings; the upper one is thru bolted to the rudder stock under the quadrant and under that, the lower one is fastened to a plywood 'shelf' at the upper end of the rudder tube with at least three bolts. Mine were 1/4" and generally worked themselves loose or widened the holes in the plywood. At the point where the rudder stock enters the hull, there may be a minor 'bearing' element where the rudder tube joins the hull. You can tighten up the system first by taking the quadrant and nylon bearings off and getting down to the plywood. Reinforce it with multiple coats of fiberglass cloth saturated in West System epoxy;. then drill new holes for at least four thru bolts; make them a size larger, say 5/16", and use fender washers and aircraft nuts to hold the lower 'doughnut' bearing down to the plywood. However if you've waited too long to do this repair, you may need to replace the nylon 'doughnuts' as I believe Warren suggests.
I went a couple steps further, since I had the rudder out of the boat, and used West System and graphite powder to 'cast' a 3-4" high sleeve inside the lower end of the rudder tube to take up the wear at that point. I tapped a couple barbed tubes thru the outer rudder tube and thru the graphite 'casting' and connected Zerk grease fittings and now can pump grease into this graphite bearing. The 28.5 has a rather large rudder for the size of the boat, so it does appear to put a strain on the original mounting system.
