Okay thought it best to update this post.
The boat came out of the water and and I was on hand to watch and learn the process, never having done that before and to see if I could help with the now dreaded, potential nightmare rudder removal.
So the rudder came out with some persuasion but all in all, relatively easily. The diagnosis was pretty instant. Dan from Weber Marine suggested that the grease the last "repair person" had used to resolve the problem had just made it worse. Swelling the plastic bearings.
So I spent 3 hours of hard yakka sanding out the scores on the