I was searching the web and eventually found an alternative to iTunes, it's a Winamp plug-in called ml-iPod
Now all I have to figure out is install it and try it out. But first, I've got to figure out why the "Do not Disconnect" Sign isn't going away despite the fact that the battery seems to be fully charged. The iPod is currently connected to my computer through a USB2.0 port, for a full hour or more now.
And in response to your post about it acting two-ways... Darn it, but it's nice to finally have a decent external HD now.