Alright. After an overly long break, I am back with an update.
I printed the clamp that holds the leather lovingly named Fenix TK22UE Holster Part 02.SLDPRT
And cut it out. (YouTube video)
And hole punched it. (YouTube video)
Then cleaned up the rest of it - and I am proud to say I did not cut myself - yet.
The 0.0625" 2 flute downcut bit worked well for reducing the shredded edge of the leather. The 0.0400" drill appears to be the size I am looking for. I have been procrastinating the next step of dying / sealing and then stitching the pieces together. I am not sure why - probably just being afraid of screwing up after spending so much time on the individual pieces. I’ll get over it eventually.