I haven't done it in this bike but anytime I've done it in the past I put tape on both sides where I want to drill and drill through the tape from outside to inside.
The tape usually stops the chipping and anything that pushes through is on the inside and you can touch it up and no one will see it.
Also good to center punch so the drill doesn't walk.
2011 Vivid Black FLTRX, 107" Rev Perf, Zippers Thundermax AT, Roland Sands Speed 7 AC, Iron Aces iPhone holder, 8" KW, V&H Duals & Black Widows, DDM HIDs, ARC 6.5's, S.E. ported heads, 30 tooth frt sprocket.
You never see a Harley parked outside of a Psychiatristís office, now do you.....