So, I'm thoroughly confused and yet at peace...
Yes, I was measuring the voltage correctly. I have no explanation whatsoever for this apparent goofiness, only more mysteries. The board had 1 inductor, 1 resistor, and 4 caps, whereas the schematic has 4 caps and 2 inductors. I can't possibly imagine what the resistor (10k) was doing or supposed to be doing. But I swapped my ground from pin1 to pin 2 and it OCCASIONALLY worked. Meaning it did what it was supposed to, but rarely. I thought this was kind of odd. Something had to be floating because I was confident the data stream was correct.
So therein lies the rub. There was a 4 pin header on the board. I was initially thinking this was some sort of probe points, but on more careful inspection, I realized this is how the radio board communicates with the main board. It appeared pin 1 was ground, pins 2 and 3 were shorted together and were data, and pin 4 was VDD. So I was probing the VDD with my scope probe and found that it was noisy. My ground lead wasn't hooked up, but I figured the Pi is grounded through USB to my computer which is on the same receptacle as my scope, so they should have a common ground and the noise shouldn't be bad. But regardless, I touched the ground clip of the probe to pin 1 of the header and magically everything worked. So... there you have it. I ran my wires directly from the Pi to the header and now it magically works perfectly. I don't know what goofy stuff they did with that resistor and the CMT2210 which seems to be wired wrong, but yet somehow still works, but when I just connect to the header it's all good. I'm super psyched...
Now, if I can just figure out how to route traffic to the Pi's webserver through the Wifi tether on my phone I'll be happy. Somehow, I suspect this may not be trivial.