Rattletrap, what you do is mount the outer bracket to the A-pillar first with a couple of sheet metal screws included with it. Then a "drilling sleeve" which is provided with the bracket kit is inserted into that outer bracket. This helps keep the drill aligned properly. Remove the sleeve and install the spotlight. Yes it's not too big of a deal to install after paint, but if I had a choice I would still drill the hole before painting. No matter how careful you are, sometimes Murphy will jump up and bite ya.
Bob