I took notice of your rudder when I was there.
The rudder appears to be glass over a solid stainless shaft.
Maybe Travis or someone else can chime in on how they pin the rudder to the shaft, but yours is loose (spins from the shaft ) Im guessing it moves 10-20 degrees back & forth without the shaft moving.
I pressed a cutlass bearing into my lower shoe. It work great. You may also want to put a stop collar on the upper shaft, inside the boat to keep the rudder off the shoe.Bill if the shoe looks ok what you could do is take a peace of round stock about 3/8 thick just to get the ruder up off of the shoe, the way it is could give a chatter noise underway.
If you are going to do that, then make sure to put a nylon bushing in between the rudder stuffing box nut and the stop collar. Otherwise you will just end up with metal on metal contact there instead.I pressed a cutlass bearing into my lower shoe. It work great. You may also want to put a stop collar on the upper shaft, inside the boat to keep the rudder off the shoe.
Electrolysis will eat out the pins in the rudder.If the rudder moves and the shaft doesn't,I would say its time for a new rudder.By the looks of the wheel,I would not be surprised if this was the case.Some times there is a small wafer of shaft under the rudder shaft to keep it off the skeg.