re: First boat: Cal 2-27, Pearson 28 or Islander 28?
If the play is in the rudder post, the bearings in the rudder post tube are probably shot. In that vintage Cal the tube goes all the way from the hull to just below the tiller head (there is no stuffing box, et cetera). The shaft is aligned by a couple of plastic sleeve bearings/bushings pressed inside the tube. These bearings get worn over time and some play results. You could get a couple-three new plastic bearings machined out of Delrin plastic, but that will probably be a bit pricey unless you can do it yourself. The "classic" fix is fairly cheap and easy, but can be a little messy; you simply fill the space between the rudder post and the tube with epoxy. There are at least a couple of descriptions of the process on the net (there might even be one on SN; Google is your friend). It's not to difficult. But does have to be done with the boat out of the water.
Never forget them. Do something to prevent it from happening again.
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