I would imagine you would just need an older version of iTunes [search for it, I'm pretty certain there are achieves of it available] If the more recent iPod firmwares work with it then you shouldn't have any troubles. Try the November 05 firmware http://www.ipodwizard.net/showthread.php?t=7369
I have a Windows ME edition, and it won't even run itunes. It's funny, because the Windows 2000 edition will run itunes, but the Millenium Edition (ME) won't. You may be able to though. ...stupid special edition OS's...