Love the idea! I've been doing something similar, but with dollar-store tumbler glasses. I use a diamond burr drill bit (for drilling porcelain tiles and stone) in a drill press to drill holes in the glass. It's a two-person job - the other person needs to constantly spray the drill bit and the glass with water. Great task for a pre-teen kid, just make sure they wear safety glasses in case something goes wrong. I've never had glass shatter and go flying, but I've had it crack. You need to be extremely slow and steady while lowering the drill press.
These burr bits will also drill through clear acrylic glasses without shattering them. Again, you need to spray water on the drill bit and go very slow.