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Exactly. If the pups get bedded down real low and then you adjust them significantly higher, you could run out of purchase pretty easily. It's probably not going to be a problem in Year 1. But by Year 10, multiple adjustments will hog out the hole.
FWIW, I don't really think of the toothpick fix as a hack. When I was a carpenter hanging and adjusting doors, I often had to repair stripped screws in a door or door jamb. The fix is to plug the hole and drill a new pilot hole after the glue dried. If this fix works for a 50-pound or 100-pound door, it outta work for a little ol' pickup.
I’m going to pay someone with the tools and know-how to do precisely thisI bought a used Ash jazz body and the former owner failed to tell me the pickup mounting holes were all punked from what looked like forcing oversized screws into the holes. Unfortunately they were too bad to salvage. I tried CA to harden the wood and the screws got a good bite, but the pressure from the foam would pull them out if I out even a little pressure on them. Same with toothpicks and glue.
I went to a home labyrinth and got a 3/8 oak dowel and drilled out the ruined wood. To get my drill depth i laid the body on a table and used my caliper to measure the overall height (thickness) of the body, then subtracted the depth of the pickup routs, divided my remainder by three and doubled that number for my overall depth, marked my bit and drilled it with a hand drill. I measured each hole and cut a piece of dowel just long enough to sit an RCH below the surrounding wood, hit the long edge of each plug with a triangle file just enough to get a shallow channel top to bottom, mixed up a batch of 2 ton epoxy and glued my plugs in. I put some glue in the hole then rolled my plug in the same glue, and used a drift and small wood block to seat them in the hole, cleaned up the epoxy that squeezed out, then filled the depression where the plug was sitting below the floor of the pickup route and scrapped it level before it started to set. Friction held them in and the layer on top helped insure a flat surface to drill my pilot hole accurately, which i did with a finger drill, AKA mini hand drill, or pin vise. I did that over five years ago and it’s still working fine.
It might depending on the glue used. Wood glue should be fine but two part adhesives may not be so forgiving. To insure your screw will back out when everything sets, put a very thin film of grease on the threads before you run the screw down.…I do want the screw to turn after the fix (unlike the screw for that strap button). Apparently it still will, then?
