Oh, and on the issue of the noted play in the rudder, it would be prudent to determine if, and how much of this can be attributed to the tiller pivot bolt. This half inch hole can easily become 1", yielding a lot of play in conditions of low weather helm.
I pulled the rudder this fall and am in the process of having .010" over pins fabricated, but most of the play was from the tiller bolt hole, so I wouldn't be building new pins if it wasn't for the fact that the old ones had cracks in them.