If you're getting characters, then I would guess that the USB port is okay as it appears to be recognized as a keyboard. If there was an issue with the port, I would expect no key presses to register at all, or for the device to constantly connect-reconnect.
That's my guess. Though I think it might actually be a combination of the two. Evidenced by:
1. USB connector was faulty. Fixed that, but it progressively degraded (disconnects at certain cable angles). Now I really have to gingerly angle it to get a connection.
2. Confirmed a proper usb connection by successfully flashing firmware (while carefully holding USB in place)
3. While holding the USB in this position, key presses are bizarre. Getting several keys outputting the the same (incorrect) characters. Most keys don't register anything.
This leads me to believe something is either shorted or not connecting somewhere.
Is there any possible way that the LED's and related FET could be effecting the matrix?
What troubleshooting process do ya'll recommend?
Thanks for the tips Pikly & Delirious!