Think I got it figured out - I was pointing my libraries folder to a location on my external drive, which help duplicate copies of the DigiX hardware files. This seems to make the Arduino IDE glitch out. All it took to fix the issue was deleting the entire My Documents/Arduino folder and recreate it with a new installation, then re-copy over the DigiX folders.
I'm getting some ridiculous hardware port errors now though - the DigiX registers as either "Unknown Device", "GPS Camera Detect", or the actual "Digistump DigiX" board with an error of "Device could not start".
When the board registers as "Unknown Device", I am updating the drivers and selecting the "DigiXAddons-v04\DigiX Driver\DigiX.inf" file - this seems to allow proper hardware registration, but as soon as I go to upload a sketch the IDE returns an error:
Arduino: 1.5.4 (Windows NT (unknown)), Board: "Digistump DigiX"
Sketch uses 10,604 bytes (2%) of program storage space. Maximum is 524,288 bytes.
processing.app.debug.RunnerException: Couldn't find a Board on the selected port. Check that you have the correct port selected. If it is correct, try pressing the board's reset button after initiating the upload.
Any thoughts?