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Drilling your own holes

I'm looking at picking up a body, but I would have to drill my own pickguard and control plate holes. I did this once with a bridge covered and just used a straight bit. When removing the cover, the screws backing out chipped away finish and paint. I'd like to avoid this. What do you do? (I realize this could be basic but I'm having trouble finding anything online)
 
And make sure you're using the correct drill bit size for the screw you're using. It seems people have a tendency to go too small, maybe under the belief that it will make the screw tighter in the hole or something. A too-small hole will significantly increase the chances that the surface is damaged from the threads mushrooming up the wood as you drive the screw in. (Not to mention that it also increases the chance that you break or strip the screw).
 
Whenever i drill in a painted wood surface i mask the area then use a pin vise to put in a pilot hole after marking my center points. It’s much easier to get it precisely centered than trying to use a drill motor.
 
Whenever i drill in a painted wood surface i mask the area then use a pin vise to put in a pilot hole after marking my center points. It’s much easier to get it precisely centered than trying to use a drill motor.
Unfortunately I only have a drill motor. I'm still partially considering calling a luthier and having it down really quick. Hate to ruin a custom paint job with the old 20v dewalt
 
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Good advice here, I wish I read this post a couple of days ago. I tried to drill new tuner holes in the headstock converting a guitar into a bass and butchered pretty badly, even with masking tape (I first filled the guitar holes with dowels, which I also didn't do too well.). I have a good guy that does that work for me, but I wanted to do it myself to save time, bad idea. I thought I would bring it to him to make it right, but decided why burden him with it, so I bought another guitar to let him do it.
 
Correct sized bits.
Counter sink.
I always lube the screws going into instrument wood of any type. I just poke the screw into a a bar of soap.
I use this drill. Came from an antique store.

drill.jpg
 
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