Thoughts on drilling holes thru good paint?

I would put down several layers of tape. Start with a small diameter bit (1/16"?) and work your way up to the correct size. I'd probably drill a single hole first, put the emblem in place (hold it with tape?) take a good squint, and mark the second hole to get it exactly level. Or draw a line on the tape using a level either horizontally or vertically depending on the stud arrangement. Then put some paint on the exposed bare metal of the holes and let it dry before the final attachment so it doesn't rust.

Or have a completely disinterested person do it for you when you're not around so you have someone to blame.
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