The pintles and gudgeons on my 1979 Oday 23 have a lot of play in them that seems to be getting worse every year. Is there any way to fix this without simply replacing them? I seriously doubt it, but I could be wrong. If replacement is the way to go, do I need to replace both? I would. I assume Rudy has them? You got it. Pintles and gudgeons can be bought anywhere. Dwyer manufactures them, but the question is, do you want to re drill the fiberglass and refill the old holes if the holes their hardware don't line up? The backup plates for your gudgeon would also need to be re-drilled. I think that I would try to get something that would fit. The hole in the top of the rudder (where tiller is attached) is also getting worn. All these worn parts add up to a sloppy feel while underway and some very annoying "clunking" when at anchor or moored. Appreciate any suggestions. What you could do to the top of the rudder is fiberglass the hole and drill in out again, or you could use a stainless steel bushing with an inside diameter that will accommodate the tiller bolt and drill out the rudder head a little bigger to accommodate the bushing.
A good idea for access to the gudgeons is to cut a hole in the center of your inside transom and install an 8'' Beckson deck plate. This access will allow you to get at both gudgeons all by yourself with no help from anyone. I was able to remove mine, re-caulk them, and reinstall them with no problem. When you leave your boat at the mooring, tie off your tiller good and tight using ropes from the stern cleats. I installed a leather chafe protection to my tiller so that the ropes don't dig into the handle and mar it.
My pintles and gudgeons are still as tight as the day they installed them at the factory. The secret is to keep the rudder from swaying back and forth at the slip or mooring.
At any rate, I would bite the bullet, install the deck plate and use silicon caulking or Dow Corning 795 which is not harmful to plastics.
For pintles and gudgeons, I would use 3-M 4200 or 3-M 5200. After you get it caulked, just get the nuts snug and don't let the bolts turn. Let the caulking set up for a day or two and come back and tighten it down good while holding the bolt heads with a wrench so that bolts won't turn.
I just installed a 4" Beckson deck plate in my fuel locker a couple of weeks ago to gain access to a small jam cleat I installed for my roller furler control line and I used Dow Corning 795 caulking which is good for plastic. I bought a large tube of it off Rudy about five years ago and it's still good. Rudy said that the boat manufactures use it for plastic hatches and port lights. The other types of caulking have chemicals that are very harmful to plastics. Good Luck!
Joe