Set it up so that when you look into the case, you see a small chamfer around the flash hole. It doesn't take much.
Also, since it indexes off the rim, given a choice, I would trim first so length is consistent.
You won't drill through the primer pocket unless you really are pushing the bit through for a long time.
Also, tap the case, rim down, on a piece of wood to knock out the brass swarf that might be left inside the case.
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