Random album artwork - Error -50

I only get random album artwork display on my 60 gig iPod. All the artwork displays in iTunes, but only random artwork displays on the iPod.
I tried unchecking unchecking "Display album art" in iTunes, and the ejecting the iPod, and when ejecting I get the error.
"An error occured while updating the default player for audio file types. You don't have enough access privlidges for this operation."
I am the sole user and administrator on this PC.
When I reconnect and recheck "Display album art", iTunes says "Optimizing artwork for iPod." Then is comes up with the error "The iPod "My iPod" cannot be updated. An unknown error occured (-50)"
Very frustrating.

I am having the exact same problem. I have a 30 GB iPod Video, and today I noticed how the album artwork is but randomly displayed on my iPod, though all my albums have their respective artwork, and the artwork shows up in iTunes just fine when going to "Get Info". However, on my iPod, only some artwork showed up, mostly for the albums I had purchased through iTunes.
I thought I'd try to disable and re-enable album artwork in the iPod preferences, and the disabling did indeed work. However, the re-enabling did not - it attempts to update the iPod saying "Optimizing artwork for iPod", and it gets about half-way there until I get an error message saying, "The iPod 'Sandra's IP' cannot be updated. An unknown error occurred (-50)." So now I have no album artwork whatsoever.
The iPod software is version 1.1.1 and iTunes version 6.0.5. Any suggestions?

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