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John, thanks for the update. It took 2 to handle the rudder as it came out so, yes, ~100lbs.
The delrin sleeve is definitely glassed or otherwise retained into the hull, either way the only method of getting it out will involve a big saw.
I pulled the bolt that retains the top stainless sleeve and serves as a rudder stop; it came out still attached to the shaft.
Given you have the same wear patterns on the Delin, I am questioning the value of the grease fittings, and grease in general. It's either to cushion the wear on the delrin, or displace seawater to mitigate the stainless corrosion, I suppose. Doesn't seem like it made a difference.
The leading idea (today) from the yard is to build up the derin sleeve with a carbon/graphite/epoxy fillet mix, then hone the surface back to oem tolerances. The only concern I have here is maintaining / creating proper bearing backlash.
If we decide to cut the old delrin out, then I have the option of replacing the delrin with the same material, or switching out to a roller bearing. These two solutions are pricy, I think.
Everyone else...feel free to chime in with comments.