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Ok, I drew this diagram after thinking about it and piecing together from examples.  Switching melts my head for some reason, and I can never 'reason it out' with any confidence.

Going to try wiring the esquire pick-up straight to jack with this in between.  

Goal:
Switch on (up) = Guitar on, tap button turns it off
Switch off (down) = Guitar off,   tap button turns it on.

it seems that switch on... it works!
it seems that switch off... it also works, but it's disconnected rather than routed to ground

So:
pushing the button (on) - changes it from on to grounded
pushing the button (off) - changes it from disconnected to on

implications of that are unclear to me.. shocking hazard? Working on this while waiting for the bits!

You switchless bastards!

It's been done for a bit, used it in a show this last weekend and decided it needed a pic.