I did for about 5 years. I just stopped wearing one about a month ago. I wore one primarily to wick away sweat on my hand; the benefit of not tearing up my fingers was a bonus. I'll answer your questions as best I can.
1. I used mine with grips.
2. I never had a problem with mine staying on. You need to get properly sized and buy a glove that is purposefully a little tight. The primary problem you're going to have is that most gloves will get slick/worn on the finger surfaces, actually giving you less grip. You'll go through a lot of gloves. You will also need to stay with real leather/cabretta gloves. The synthetic gloves are actually a sock-like material with an overlay. That works really well in golf, but not well at all in bowling. You can go through a synthetic glove in about 2 games. A leather glove will last you several weeks, even months with proper care. The best place to buy is in bulk on eBay.
3. I had to take my inserts up 2 sizes each.
Jess