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Drilling holes for strap buttons

By the way, if you don't trust your eye to get the side-to-side angle of the drill bit correct, you can put a piece of masking tape on the top of the horn. Place one edge of the tape to show the path of the hole needed to get the button flat with the tip of the horn. Use that edge of the tape as the guide while drilling, looking down on it.
 
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Thanks for all the suggs, folks... I really appreciate it! I've decided to proceed by hand and acquired the appropriate tools. Probably will do the deed next weekend if I'm not on-the-road for my day hustle.

In the meantime, these Warmoth bodies were finished by a 3rd party and have a thick poly clear coat. Any chance using a spring-loaded center punch to make a centering divot could cause cracks in the clear?

Thanks again!
 
Any chance using a spring-loaded center punch to make a centering divot could cause cracks in the clear?

Yep, it might. I love the spring-loaded automatic center punches, but some of them have fairly nasty springs. They can crack hard thick paint. In this case, use an old-fashioned non-automatic center punch. A steel rod with a point on it. Tap on it lightly with a hammer. You don't need a very big "dent".

You are probably drilling with a #36 bit. That's the correct size for a #6 sheetmetal screw in a fairly hard wood. After drilling the hole, cut a small countersink at the start of the hole, maybe 1/4" diameter. Use a countersink bit with a sharp point. This will keep the paint around the hole from peeling up as you drive the screw in.