re: First boat: Cal 2-27, Pearson 28 or Islander 28?
Often a good bit of play can be found in the tiller head itself.. so a careful look for the source is in order.
New bushings would not be that big a deal, esp if the stock itself has not worn too badly.
1984 Fast/Nicholson 345 "FastForward"
".. there is much you could do at sea with common sense.. and very little you could do without it.."
Capt G E Ericson (from "The Cruel Sea" by Nicholas Monsarrat)