How to drill Tele neck woodmount holes?

Run screws through the body just far enough that they're barely poking through, then put the neck in the pocket so that it looks right and everything lines up. Then give the neck a little bang with your hand to mark the back of the neck with the sharp parts of the screws.

Should give you a pretty good idea where to drill.
 
What I do. Is put the neck in the pocket. Install a crappy old High and low E string. Line it up.good. Then clamp the neck in place with a padded squeeze clamp. Then set the drill bit depth with tape and drill through the body holes into the neck.
 
Oh wait do you mean body mounting the neck pup?
Hum....ill have to think about that.
Ok few mins of pondering. Run screws through the pup. Put the pup through the guard tape in place. Put a wet drop of paint on the end of each pup screw. Then set the guard down in place. Then lift it straight up. Should leave ya marks on the body.
 
Oh wait do you mean body mounting the neck pup?
Hum....ill have to think about that.
Ok few mins of pondering. Run screws through the pup. Put the pup through the guard tape in place. Put a wet drop of paint on the end of each pup screw. Then set the guard down in place. Then lift it straight up. Should leave ya marks on the body.
I like that idea, but I don't think paint will be clean enough for a good mark. Perhaps some drywall nails cut to a shorter length?
 
If I were a braver man I'd figure out a way to make them adjustable from the rear with a nice recess so it doesnt scrape up your belt
 
I usually align and drill pickguard holes last with everything mounted and the neck bolted on strung up and the 2 E strings on.

With the pickguard location already set It might take some trial and error. With a small block and some light double side tape prop it up through the pickguard cutout. The leads may prevent pressing it down flat in the cavity bottom. Light enough tape you can nudge it and keep it attached. Then nails or a drill bit to mark the holes.

Another slightly wonkier option. Place the pickup in the template cutout off the guitar, then mark and drill the hole locations in the template. Then attach the template to the body with a few pickguard screws. Should be able to drill the holes in the right place on a drill press that way assuming its reasonably true and bit isn't wobbly.

I was going to suggest in your other thread about 3D printing to make pickup locating guides. There is a guy on reverb who selling them for direct mounting humbuckers.
 
Sorted it out. I just used calipers to measure the exact distance between the the screws center-to-center and then I left the entrance to the holes slightly oversized to allow for some wiggle room
 
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