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Jim I see two issues here.
Oil an glue don't go well with each other, so that would speak for oiling it afterwards.
Leather thats been treated, will become softer and possibly more elastic, which...

Jim it works like a cushion.
Probably to get you that second ankle.

Newer paddles have something else inbetween I can't find the right english word for.
Maybe a thin sheet of moss rubber would...

Hi Jim!
I'm just about sanding off the glossy surface from strop leather.
Guess that there is some spray can finish on your leather as well.
IMO it has to be taken off. Then the wrinkles will b...