We use the self tapping screws for Wheelwriter keyboards. I'm pretty sure the screws are tapered. When they are tight just the very tip will stick through the top of the barrel plate. We use an electric screwdriver with a torque limiter, so it ratchets before you can over-tighten the screws. I'm pretty sure the hole we drill is smaller than the screws, it's just there to keep the screw going straight.
When we refurbish a whole Wheelwriter typewriter we try and avoid having to rebuild the whole keyboard, and drilling the plastic with keytops on is kind of dangerous, so we just use the soldering iron to make a divot and then use the self tapping screws. No need to drill anything and no need to remove the keytops.
I can probably grab some pics tomorrow.