Are the screws you've been using self-tapping, meaning the threads are angled and sharp?
I considered a similar approach but wanted to test out my mechanical abilities with the tap wrench. Drilling the hole takes a long time for me, while the tapping process is much quicker.
Looks like the Kapton tape will be getting benched for future COB mounting; the stuff I have is no good with EZ PicoMate cords.
if you can afford it try to invest in drill press, around $80 for a nice one on amazon etc. Not just for taps but they come in handy for many things. They drill slow and straight, and bits last much longer. Hand drills I always used to break those small bits due to my unsteady hands and high speeds lol. RPM is slower but it cuts through alum like butter and drills the holes in a few seconds.