I had similar problem with mini iPod (iTunes wont work) & I done the following 1 Used friends XP PC & loaded iTunes ,Initilized & updated iPod.
On my own computer (WinMe)
2 Downloaded Winamp & iPod plug in(free),which will allow you to drag & drop files(mp3) into iPod.
3 Use musicmatch jukebox to convert music files from CD (wav) to mp3.
4 If your using w98, you also need to download "mass storage drivers" available from redchair software or possibly some other source.
Incidently,this arrangment works also on the slower usb1 connection.