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Filling a screw hole and redrilling/shifting screw hole a tiny amount - best method?

Hello TB luthier hive-mind. I have a rectangular pickup mounting ring that is just ever-so-not-squared-up where it should be. It's close enough that I can pull the screws, shift the ring to the right spot, and still see all four screw holes. But the holes in the body are slightly off, so as you tighten everything down, the ring gets pulled out of square. It's the sort of thing that I'd imagine wouldn't even register for most "regular" folks. But it's driving me absolutely insane when I look at this thing.

So.....to try to calm my OCD I'd like to try to fix it. Given the super tight tolerances, I'm thinking my best bet at this point is to fill the holes and re-drill. I'd considered the "toothpick trick" to fill the old screw holes, but I'm worried that unless the new plugged surface is perfectly flat, the drill bit could wander and I'm right back where I started. So then my mind went to wood filler - I could fill the hole, build it up a little over the top, very carefully sand it flat, and have a good spot to mark with a punch and get a clean new hole. But - could that also cause some "bit wandering" given the difference in density between the wood filler and the body wood?

Thanks in advance for helping me prevent an eye twitch every time I see this pickup ring, lol.
 
Wood filler is useless for any kind of stressed application.

First, drill out and plug your misplaced holes.

Then, make yourself a drilling template out of aluminum, with the holes exactly where you want them. I'd say for small screw holes, a 3/8" or 1/2" thick drill guide plate would be about right.

Then, clamp the template to your workpiece, square it up just so, and drill the holes.
 
Can you drill slightly larger holes in the mounting plate and just tweak the plate in tightening?
This.

Unless the plates clearance holes are countersunk with flathead screws, open up the clearance holes, put the plate where you want it and then tighten the screws.

If it is countersunk with flatheads, get button heads.
 
No wood filler. A big ol' fat round toothpick (mid portion) glued / wedged into place should work. Once plugged and the new holes are marked, I tap an indent with a fine-tipped awl to center the drill bit...I use a Dremel with micro-bits and freehand the pilot hole.

Simpler method, as mentioned, is to modify the screw holes in the mounting ring. A few swipes of an xacto file should suffice.

Riis
 
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Drill bits will try to wander from harder wood to softer wood.
So you need to drill out and dowel if possible.
Flush off the dowels with a chisel (properly sharp!)
One thing that I found that helps with this are Vix Bits - self centering bits that would be useful in the OP's application since it sounds like he's mounting a metal pickup ring to the bass body. These are most common for hinges, but useful for anything needing to be mounted accurately. Much better than a centerpunch or awl.
Vix Bit for hinges
 
Right. I had a tailpiece off-center by 1/4". Probably made ABSOLUTELY NO DIFFERENCE to playing but everytime I looked at it, it bugged the heck out of me. While I couldn't hear it, I could "see" the string slant. Every time I looked at it.

You just need a toothpick (unless it's a LARGE diameter screw!) and glue. After glue dries, shave the stub down flat and us a "centerpunch" (any "pointed tool") to create a "dimple" at the right position to start a drill bit. Should get you within 0.5mm of the "correct" position easy. It's wood ... You don't need machinist's tolerance.

Now it "looks right". Even if I can't play it any better! :p
 
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Super glue and baking soda. Then do the indent for the new screw hole with an awl. I've done this many times. Also have gone the toothpick route but usually prefer the first way.

BBB

Well, it works on nut slots and is apparently durable. I just don't like CA around guitar finishes unless doing drop-fills or glue & dust on fingerboards.

Riis