The smaller the hole the easier the fix. You drill the hole out to the size of your dowel and when you insert the dowel plug you bring it out flush with the shell, not the wrap. Then you cut a piece from your wrap with a hole saw. If you don't have matching wrap (and new wraps do not match old wraps) you can do this by taking the wrap plug from behind the lug. People also get replacement wrap from a beat up "project drum" doner.

This will make your vintage piece look as good as it possibly could, but if you are going to be honest with a person you sell the repaired item to, you should disclose that "the holes have been meticulously repaired with the correct wrap" or something to that effect. People know how to look for this type of work when they expect to be buying a "perfect example."

regards,

Gary