Welcome to the madness.

Simon's suggestion of having the kit checked over before sending is very sound, PBG have customer service that is second to none in this space.

As for shaping the headstock, I've done a few now and just use and old school hand jigsaw/fret saw to get close and then hand sand up to the line.

My wife and I walked up that little hill you have a couple of years back on an incredibly hot day, well worth it for the view though, nice part of the world