Josh, (and to all who share this problem), I think I have found a solution.
After searching through every support tutorial available and reinstalling itunes many times, I decided to take a look at Quicktime. Turns out it didn't recognize my audio driver, or the "enhanced features" or something like that.
Anyway, try this:
Install iTunes (or have Quicktime installed at least)
Start Menu-->Control Panel-->Quicktime
Under the audio panel, click "Select Audio Playback and Recording Devices" (mine was flashing blue, like a sign from God)
Now just re-set your computer's audio driver as your playback device and you should be good to go!
I hope this works for you
Andy