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As you go through these watches Tmac you will see all sorts of weird and wonderful things people have done to try and get them to work. You are quite correct about how to effect a proper repair. Take measurements from two opposing holes so you dont lose the hole centre, drill out all the bad metal and plug it, then drill a hole the correct size. Do you know what type of jewel fitting used to be there? This is where my knowledge comes to an end as if it was a rubbed in jewel I am not sure how you would re-create that type of setting.
Maybe someone else on here knows?