I-Pod No Longer Synchs

Since upgrading to I-Tunes 5.0 (and 5.0.1.4), I can no longer synch my Ipod. I must manually add songs and update playlists. When the Ipod is set to automatically update songs and playlists, during connection ITunes flashes "Ipod is Updating", but nothing happens. I can have it connected for 20 minutes, but no songs or playlists are updated. Anyone else have this annoying issue? I have a 4th Generation 20 Gig Click Wheel Non-Color IPod running the latest 3.1 software.

I have the same problem with my iPod 40G click-wheel, when I upgraded to the new version of iTunes 5.0. I thought the hard drive was corrupt after reinstalling operating software, iTunes and resetting the iPod. Brought it in to the desk at the Apple store and received a new iPod, however the problem still exists. I am running iTunes on a Toshiba laptop Windows XP Professional and the USB ports are working fine...I can perform a manual update to my iPod, however when trying to sync I get various errors with the following description --- Unknown error updating iPod disk (-50) and Unknown error updating disk (-69). Then the whole process freezes and I have to end task to stop the iTunes software. My novice deduction leads me to believe that this is a problem with iTunes new software.
PLEASE HELP!!!

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