Does anyone have any tricks for removing to "wobble" out of our 30+ year rudder gudgeons / pins? Does one wear out but not the other? If so, which do you replace? Is there any creative ideas for thin plastic or tefflon shims that people have tried and found an improvement?

Yes. Have new pins manufactured at a local welding shop (bring the old ones). Mine cost $20Cdn. Apparently commercial boat shaft was the perfect size - they just cut the top plates off the old pins and welded them onto the new ones.