#1
I put straplocks on my Squier Jag yesterday, and I noticed that the original screws have a significantly larger diameter of thread than those that come with the straplocks. I tried putting the Squier screws through the straplocks, but they didn't quite fit through the hole, so I used the Schaller screws and, though they took a bit of convincing, I got them to bite without too much trouble so I didn't think much of it. Now, a day later, they've already worked themselves loose and obviously I can't trust them with my strap.

The most obvious solution I can think of is to use the longer Schaller screw, for an extra centimetre or so of grip, but I'm worried that it'll still work itself loose again and just leave a larger cocked-up hole in the guitar, or that I'll need a pilot hole (I don't have a drill; the body is basswood, so I don't know that I'd need a pilot hole). Is that a good idea or should I enlarge the straplocks' holes to use the original screws (which I've no idea how to do)? Or something else?
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#2
Get a toothpick or another thin piece of wood (shave the side off a pencil, for example) and break it off in the hole. Put a tiny dab of white glue or clear nail polish in the top of the hole. The glue is just to add a little resistance to the threads so they don't wiggle back and forth when you move the strap, you are not gluing the screw in. A properly done shim does not need glue, the friction fit is enough to hold both in. Gluing the screw in just makes it impossible to unscrew without ruining the finish and/or taking a chunk out of the wood.
#3
Put a piece of toothpick with a little glue in the hole. Fixed.
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#4
Cheers I'm not entirely clear - from "shim", I'm taking that the piece of wood goes alongside the screw, as it were. Is that right?
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#5
Yes, the idea is that you just need to wedge something in with the screw so that there's enough friction for it to bite and be held by pressure. Once the shim is in, the friction between the screw, shim, and the sides of the original hole should be enough to hold everything together securely. If it's not, you need a bigger shim. A shim that is too large will cause you to force the screw in, possibly cracking the finish or wood. If it feels snug but not overly difficult to screw in, you've got about the right size.
#6
Toothpick or match stick both will work great. I always use a small dab of wood glue on the tip of the shim to make sure it stays put. I don't think I have a guitar without a couple of screws done this way, need to do another one in the Peavey Patriot right now, noticed it a few nights ago...

If you use a match stick, trim the tip so it has a little of a point for a better fit. After you break it off carefully trim it with an xacto knife to remove anything that sticks up.

Shim -

Shim is a term used a lot in several different fields, usually it refers to a thing slab of material place between two layers to raise it a little, like the bottom plate of a building, you shim it to get it level. Sometimes the front end of a car when aligned needs a shim or two in certain places to set the proper angles of the front wheels. I've never heard of this particular thing called a shim, but I guess it will work...I've used it for guitars, door hinges, chairs and tables, all kinds of things made of wood that come loose.
Hmmm...I wonder what this button does...