Several solutions and one open question:
- Drilling holes in glass. I build a "dam" around the hole site and fill with water. Then use a diamond particle "drill" in a Dremel or even an electric drill. I use plasticene modeling clay to hold the water. Key is to "wear" your way through - push only gently. (If you have to drill through on a verticl surface, then a special water containment "puck" or else a water squirt bottle (2 person job) might do. Water cools and damps vibration. An old 19th century trick.
- Gluing teflon, silicone. Flash surface with the inner cone of a hot torch. A butane torch works well. (small flame.) Play over surface to oxidize it.
- Gluing rubber, like the soles of modern shoes. Modern shoes use 'molded' soles which wear out quickly - even 0 shoes you will see this. (Rockport World Tour, Ecco Seawalker.) The open question is how to put a repair on the sole to fix rounded over wear. "Shoe Goo" not good enough.
AFAICT, a good approach would be a one part or 2 part castable urethane. Fill with strengthening particles like fine silica for wear resistance? How to get a good bond to a rubber sole which may have oil in it?
It's challenge for the glue expert - Probably sanding the sole, then a layer of "Gorilla Glue", then butter on a filled, castable urethane.
Although these are not specifically 'electronics design," much electronics needs packaging, and these bonding issues may be relevant at some point. As a gluing challenge, the sole fix is tops. The wear properties of automobile tires have not been achieved with shoe soles, IMO.