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How to cut a new strap hole

You can drill a clean hole in leather, but you need to use a brad point bit, and the leather has to be clamped down to a piece of plywood backing.

I'm not sure what kind of bit I used is called. This is the culprit along with the clamps and baseboard that enabled the process. As I said, "Mission Accomplished." However, once the strap is in place, you can't see the hole at all. And that's doubly true when I slap on a rubber gasket to function as a strap lock for twenty cents versus twenty dollars. So all this effort to pretty up the hole is pointless.

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