You sound like you are after some alternative software to transfer files to and from your IPOD.
Look no further:
http://redchairsoftware.com/anapod/
Yes you have to pay a small fee to get it, but its a rather superb program. It uses windows explorer and you simply drag and drop songs into the window to commence transfer. All you need is for the drivers for the IPOD to be installed and then use this software for transfer. I have the creative version myself and its a lot better then using media player etc to transfer songs to it
