I emailed the gents at Falbatech and they let me know that everything is by design. Since the case is compact you quite literally have to drip solder down into the hole to make the connection.
One other fun bit of info: Once you solder in the switches there's no way to access the push button on the Teensy…\
I ended up having to reach in with the allen key provided to disassemble the case and probe around until I hit it.
A photo of the right hand half that I completed. Now onto the left side.
Why not flip the teensy?
This turned out to be a non issue once I programmed the Teensy the first time. The firmware that Massdrop recommends has a software button for the teensy that I'm using now.
To me, the mounting plate looks thick enough to hold the switches too far away from the PCB. That, and/or the PCB doesn't go far enough into the plate. This looks like a questionable design decision, placing form over function. "Dripping" solder into holes is definitely a bodge - but hey, as long as you can get it to work, it works.
Total bodge. I'd probably recommend against this case in the future. Their regular or the acrylic case would save a lot of hassle. There are visible seams when the case is together that would be fixed with some strategic sanding of the PCB.
Right now, I've been using the keyboard full time at work 4 days and am generally enjoying the heck out of it (or at least I'm telling myself that to justify the purchase).
There's one, glaring issue I'm having with a few of the keys though: Certain keyswiches aren't responsive. Some need to be hit extra hard while some will register a double keypress. I tested the continuity of the keys while assembling them and they all showed good connectivity. I'm going to spend some time this weekend debugging it further but was wondering if anyone had any suggestions to debug hardware like this (I'm on OS X). This is my first real experience with hardware, I'm a software guy by trade (First step is going to be to use a different system, obviously.)