Ok @tony So this happened again. Looks like 9 days after a full charge (based on the timestamp of my last post). It happens in the middle of typing. I'll be typing some text and it will stop sending characters. No buttons will work, except for pushing the mouse joystick, which will cause the light to flash once quickly with each "click". After letting the twiddler sit for a little bit, I can push the mouse joystick to wake it up, and it will give the usual three quick flashes and let me pair with my laptop. Once It's paired, it will sometimes allow me to send a couple characters before becoming unavailable again (and sometimes it just won't be responsive at all).
I have been taking random power level readings from the twiddler when I have used it just in case. The last set of readings, were:
vcc=96 <--- this is immediately after charging 9 days ago
vcc=96 <--- this is about an hour prior to the issue happening this time around
I don't know why the power level went down and then back up again, but some fluctuation is normal after letting it sit for bit. Note that I did not charge it at all between the first and last of those readings.
Thanks for your help!