I've had almost no problems since I got a drill sharpener that's capable of splitting the point. Oh, and I drill them on the lathe, 50-50. I'm using maple for most plugs, some AYC for poppers. The maple is the most challenging for drilling.
FWIW, I drill the blank first. Then I center it around the hole cuz the hole is always off at least a little bit.
I found that the drill tends to try to wander less at about 1500 rpm compared with 500 rpm.
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