I think it can be done, however, your going need something other than itunes to do it.
When I typed in alternative to itunes, in google I found this thing called anapod explorer.
http://www.redchairsoftware.com/anapod/ctable.php
The thing that really makes this standout is that it has windows integration, so Im guessing that when you go to my computer, the ipod looks like a physical drive. check it out and let us know if this works out for you.