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Once the plastic has started to break down and oxidize their is very little that can be done. The oxidized layer can be sanded and removed then...
They look pretty sturdy...they must go in fairly quickly...the assembly line would have dictated that. Maybe a special pair of pliers?
Strip caulk is good, it doesn't harden. ProForm makes a product called dum dum, and the 3m stuff is very good as well
The old golf grip installation trick...very clever 99..
My two cents, I believe my first 66 had the 3 spoke, and would be my choice, to me it looks more performance oriented...good luck!