[Quiet Man Cometh]

Alright, so got some help from a friend of mine who works in tech support. No, there does not appear to be a way to get music from an iPod back into iTunes as it is now. I was able to do it using something called Media Widget. It seems to have done the trick though it's slow since the trial only lets you move 5 songs at a time and I had to keep opening the wizard until I got all my 300 songs moved over. (Not the biggest library in the world but big enough to be annoying)