Id like to make a suggestion from having done dozens of these over the years all the way back to the days of Bill Davis.

When drilling your holes run your drill in reverse through and past the clear coat, even all the way though. Doing this will ensure that the sharp edge of the bit will not grab and chip the clear as it passes. It seems counterintuitive but it works really well and takes some of the angst out of the process.

If this has already been discussed I apologize. Hope this helps.

No need to be ashamed my friend. That’s why we are here, to help each other out. It does work on larger holes though most holes you will need to drill out on a playfield will only require on pass from my experience. Stepping up in bit size as you know is always the safe way to go on larger holes.

Agreed. If you can drill in advance that is always best. Even so drilling holes for t-nuts and other posts can be done this way even in a single pass from my experience. If the holes are pre-drilled the main goal is just breaking through the clearcoat without damaging which is where these techniques come in very handy.