Thoughts on drilling holes thru good paint?

Ive done this, and never chipped the paint yet. You are correct with laying the tape down. I however was using a brand new good quality drill bit so I didnt have to put any excess pressure on the panel. I also did not dimple the metal. I just marked and drilled. I didnt have any problems with the drill bit walking.

I dont know of any other ways to do this, other than the direction your looking. Perhaps others will chime in.