PILOT HOLES PILOT HOLES PILOT HOLES!!!!
how was i not doing this already?! by:
1 drilling a small pilot hole,
2 then a slightly larger one in it,
3 then a slightly larger one,
4 then going to the 1/2" bit,
5 then flipping over and drilling from the backside after getting about 1/2 through with the big bit.
6 clamping on with the punch and wrenching away till you hear the pop (Punch/teeth on the CP side, die on under side, makes the hole's lip go downward and finishes 100% ready for hands to be sliding on it and not getting scratched or cut)
using this method has seriously expedited the drilling the starter hole for the punch, it has allowed to me place the holes very accurately as well and minimized walking or having to apply insane amounts of weight behind the drill. This takes a little time still, but is no longer a PITA during any of the steps.
The knockout punch did wear out after 13 holes though, so plan on either going very carefully while tightening, or only getting about 10-12 holes out of one before having to replace it) if you are working on 14 gauge hardened steel like your old buddy, OP