So I'm putting the finishing touches on everything so I can post it all online for your consumption, the project is done though, so I'm calling this a win. I created a set of labels for PICxie:
That should be 1:1 scale by the way, to give you an idea of the size of the thing. It ended up being a bit bigger than 1"x1"x1" simply because it's hard to fit everything in to a package that small and the headers actually take up a LOT of room. The headers I'd originally chosen was just too big, so I went with a smaller one, but it was about 4mm longer. Final dimensions came out to be around 1.14"x1.14"x1.58" which is still very tiny, if I removed the speaker I could definitely fit it within a 1" square case, but I want the speaker so it stays and the case gets bigger.
I'll post a longer update with many more details about the process after midnight. :)