It won't be possible for you to do the same with the ErgoDox, since the Teensy mounts on the top side; you could however ofcourse mount it on the bottom but then the reset switch would not be accessible.
I just bridge the two reset pins anyway. My current ergoDOX is a single hand with an upside-down mounted teensy.
You could forego the 3.5mm jack and just have a wire. You could even panel mount a jack of some sort to the "front" of the case from under the board. The possabilites are endless! Or you could simply have the 3.5mm jack on the underside.
Basically the ergodox was designed with all the components sticking "up". If you flip it, the teensy goes on the "bottom" of the LH PCB, and the port expander on the bottom of the RH PCB. You'd need to forego the USB connector and just use the one on the teensy (it's easier, and what I ended up doing). Then you solder the switches to the "top". The entire assembly would look great (only switches and plate visible from the top, and only connectors come out the front.
You'd have to do some careful measuring, to see how much space the bend eats up, but you can have it all lasered at one place, then the two sides bent down at another. I like it!
The only thing you "lose" is that it has to be at least tall enough in the back to cover the height of the teensy, plus add a little room so you odnt press the rest button or USB port by mistake. If you don't use pin headers, the teensy can be very close to the PCB: so it's not an issue.