Anyone ever DIY Patched a Leather Sole?

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I have a pair of shoes that I've had going on close to 20 years now-I got them when I was in high school.

In that time, I've had two full soles and two half soles put on them. I should give them up, but they're the most comfortable pair of dress shoes I have and I don't want to(plus it's a point of aggravation to some family members that I do just keep fixing them, and like the fact that I'm fixing rather than replacing :) ).

As my leather sole shoes have a tendency to do after some wearing, these have a hole in the left sole about the size of a dime and the right is starting to show some distress there. The cobbler who's always worked on them looked at them and said "Sorry, I don't think they'll take another one-just wear them when it's dry until the hole gets too big." I'd like to at least keep it from getting worse, though.

I'm wondering if there's something I can fill the hole with-not necessarily to plug/seal it but just to keep it from wearing more in that spot.

Has anyone done anything like that themselves before, and if so how did it work and how did you do it?
 
Tough application, nothing will be great, but I would try 3M 5200; tough, flexible, very adhesive and should bond to prepped leather. Cant think of anything else that is readily available...
 
and if not then try to find an old time shoe repair place and get new soles is my suggestion.
Per my OP, the "old time shoe repair place"(which, BTW, has been in business since the 1940s and is run by the grandson of the original owner) has resoled these a number of times. The sole leather is the 5th that's been on these. As I said, it's had two full soles and two halfs between the fulls. The most recent repair is a half sole. The shop quite literally said they don't think they can sole it again and didn't want to try.
 
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