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You don't have verticals movement now, do you? If not, that bolt is not keeping the rudder up. Looking at it, it appears that the rudder shaft is in 2 sections and you seperate them by removing the nut and bolt. That said, I wonder what IS keeping the rudder shaft in place? Why is it not leaking? The rot on the wood seems to be from water from above (rain) sitting on the sole not sea water. There must by some type of stuffing box that the shaft passes through. I see that there is a seam just below the nut. I'm thinking that there is an integral collar on the bottom shaft that rests on top of the stuffing box that keeps it from sliding up or down.

Now the important questions: if you probe around the area just on top of the piece of wood, does it seam that there is wood under a collar on the shaft or does the shaft go straight down through the wood? Can someone pull up on the shaft so you can see if a space appears between the wood and a collar molded on the shaft. If so, the wood IS keeping the shaft from sliding down and it's removal could be problematic. You say that the wood slides around from side to side. This causes the shaft to do the same. So this wood is not caulked down. Yet no water comes through? I think you need to figure out the answer to this question prior to disassembly. I don't think that bolt is keeping the rudder in the boat by itself. Something is. What? If that wood is what a collar is resting on, it's removal would be a problem. You could let water in. If want to know more first. Maybe take it to a beach and beach it so the rudder would be supported underneath? With calipers, find the diameter of the shaft so you can drill a correctly sized hole in a new piece of wood at the ready to install in place. Using caulk as an adhesive, adhere the new wood on the sole to stabilize the rudder.

Good luck,

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