So, a lot of progress has been made on the RPi front, though none of it good!
Setting up the I2C to be automatic, using a startup script:
For some reason, PureData refuses to recognize the USB sound card and crashes every time. The sound card works when I play a sound clip in the terminal with aplay. Since the prospect of programming logic in PD is daunting at best and nightmarish at worse, I've decided to just go with python since all the code exists for it already. In python I've successfully programmed a key scan program to read all the GPIO buttons and report which buttons have been pressed on the I2C LCD.
HOWEVER. VNC viewer will not play nice with pygame! And so far pygame is the best candidate for sound manipulation with python. I'm not liking python anyways. Maybe its time to switch to Java? I'll have to learn I2C in Java because I won't have the sample code to rely on.