I finally have 2 solid theories for the small holes:
Theory #1 - He had a room-mate or workmate he didn't trust. He was thinking of getting a really nice monitor and the only way he felt he could secure it was to thread cable through it many times. He said "security" in the post and also mentioned buying a new screen. So it was a wild-shot idea he had while drunk one evening.
Theory #2 - He was going to go for a decorative look and one of the holes would hide a small camera. I remember plenty of monitors that had lots of "holes" of varying sizes in a wavy pattern across the bezel. This was back in the CRT era when Gateway was still a thing.