Thoughts on drilling holes thru good paint?

I am adding some Commando emblems to the front quarters on my 65 and will have to drill some holes for the studs. The car has some really nice paint on it and I am hoping to avoid a big chip of paint coming off.

:banghead:

I was going to place some masking tape down before I drill and I know I need to dimple somehow to center the drill point (bit afraid to center punch,lol). But small drill then bigger or drill right to size. Anyone had to do this before on nice paint? Thoughts, Ideas, horror stories?