Spent a few hours shaping the headstock... turned out reasonably well for a file and sandpaper job...
I've included a shot of my jig to hold the neck in my vice so it could be worked on. handy thing is it also allows to be reasonably sure the filed/sanded edge sections are square to the front face... and nil vice marks on the headstock (which my vice is easily and perfectly capable of doing.. it will crush wood if you want it too)...
Also a couple of pix of my pine tuner test template drilling trial, and yes the pine is thicker than a headstock so the ferrules don't sit low enough, but it was only to prove drilling measurements and spacing.... The exact same drilling (as close as possible) was done to the headstock...