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You do need to be careful where you fit the neck strap pin though - into the block (and not just through the wall of the guitar) but also in a sensible place to the guitar balances ok.
iirc @ICBM knows more... (as usual )
Be very careful with a hand-held power drill - if you're unlucky and it 'grabs' the wood you can end up splitting the endblock and the sides of the guitar.
I use a hand reamer and a 1/2" drill bit held sideways in a pair of mole grips - it looks crude, but actually gives you full control of how much and how fast you're cutting.
Drilling into the neck heel also needs care - some guitars have metal bolts hidden inside and if you hit one you're in real trouble. Check thoroughly inside the guitar first. Usually the best place is about halfway up on the treble side of the heel, *not* on the back of the heel cap.
"Take these three items, some WD-40, a vise grip, and a roll of duct tape. Any man worth his salt can fix almost any problem with this stuff alone." - Walt Kowalski
"Just because I don't care, doesn't mean I don't understand." - Homer Simpson
I'm no woodwork expert, but that is way too coarse a tool to use on a guitar body. You'd be better off with a brace and bit and/or hand-held reamer.
Incidentally, most Taylor acoustics have a bottom strap pin that removes easily to leave exactly the right size hole for an end-pin jack socket.
I'm just getting frustrated at the lackadaisical tech - he did finally reply but is away until the middle of next week <sigh>
I'll probably just cool my jets.
But to understand better (because why not) - would you use a hand reamer to open out the hole (they seem to come as 3-12mm commonly) then a 1/2" drill bit to get the final size?
"Take these three items, some WD-40, a vise grip, and a roll of duct tape. Any man worth his salt can fix almost any problem with this stuff alone." - Walt Kowalski
"Just because I don't care, doesn't mean I don't understand." - Homer Simpson