I toner transfer the labels as well.
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You can DIY at home, but it's a lot of trail and error - took me 1 week and I'm a Mech Eng - and in the end it's never going to be as good or as easy and getting it made.
As for the power connnector ... the one I am using is a part from Adafruit or Sparkfun ... not sure which, and the legs do not seem to require a hole any larger than the 1.2mm hole that is standard on the Adafruit perma proto boards.
The blade pins on the audio jacks might be wider than 0.052", someone will have to measure them.
