Tracking file usage (video) by directory?

Support
#1

I have a bunch of tutorial videos on an external drive and I want to keep track of how much I’m watching them, and what specific topics I’m spending the most time on, e.g “Cooking”, “Music”, etc. Most of the video titles are generic (Introduction, Part 2, Episode 2) so a long expression with a bunch of keywords sadly wouldn’t suffice, at least not without some bleedthrough between topics which I want to avoid.

The only idea I have would be to track files by what directory they’re located in.
So you’d have one category, “Cooking”, that watches for any files opened from within this directory:
C:\Users\USERS\Desktop\Study\Cooking
Is it possible to set something like this up?

#2

use bulk rename tool to prefix (foldername) and programmatically add the regex rules
for example “cakes|chicken” etc.

Option 2:
open a project on upwork and get at customized as per your liking.