Ipod loses artwork from random albums

I have a black 160GB iPod Classic with the 1.1.2 software synced to a Macbook Pro running iTunes 8. All ~60000 tracks in my iTunes library have artwork that I have manually added, and I sync about 9000 of these tracks to the iPod. All the artwork can be seen in list, grid, and cover flow views in iTunes, but after upgrading to iTunes 8 I've noticed that some albums show up with the generic "gray square with a musical note" image on the iPod, suggesting they don't have artwork. After reading through this forum I tried unselecting the "Display album artwork on your iPod" option, syncing the iPod, reselecting the option, and syncing again. While this didn't fix the problem, it did change which albums were missing artwork. Some that had been missing were now back, while others that used to have artwork were now blank. I've also tried rebuilding the iTunes artwork cache by selecting "Get Album Artwork" from the Advanced menu, but this did nothing as far as the iPod is concerned. One other fix I attempted was to switch to manually managing the iPod and delete the ArtworkDB file on the iPod via the terminal. Upon rebuilding the artwork database the iPod still had missing artwork. I've now restored the iPod and am in the process of copying all the files to it anew.
I've seen other posts that relate similar experiences, but haven't noticed any reporting this seemingly random loss of artwork. The issue is specific to the iPod, as iTunes displays all art properly. I've spoken with several friends who have had similar issues since upgrading to iTunes 8. Any hints, or am I stuck waiting for iTunes 8.1?
Message was edited by: deadward

*Why is artwork not showing on my iPod when it's there in iTunes?*
iTunes will display a cover in many of it's views provided at least one track from the album has embedded artwork. The iPod appears to load only the artwork from track one to create the cover flow and album views which means that it can sometimes fail to display art for albums even when you can see the art in iTunes. Further, when tracks are played on the iPod, artwork is displayed if and only if it exists in the currently playing track, so track one may show art while track two does not.
*How to find tracks without artwork*
To find all the tracks without artwork so that you can update them you can try http://www.stum.de/itunes-find-tracks-without-artwork/ for Windows or http://dougscripts.com/itunes/scripts/ss.php?sp=trackswithoutartwork for Macs. Use Google, Amazon, Discogs etc. to locate relevant jpeg images. Ideally these should be square, 320x320 pixels or above and borderless to give the best results in the various menus. If you have artwork for some tracks of an album, but not others, find the album in the main music folder, select a track with artwork, right-click (Option-Click for Macs) on the art & click copy, then select all the tracks of the album, use CTRL-I or Command-I to *Get Info* and then paste the image into the artwork box.
I say 320x320 because I believe (from using TouchCopy) that it's the size used in the iPod cache so if you're going to crop or resize you might as well work to that size. Otherwise 200x200 is probably good enough.
*Rebuild artwork cache*
Sometimes the artwork cache becomes corrupt and fails to show correct artwork, even when this is properly set up in iTunes. To rebuild the artwork cache, connect your iPod to iTunes. Locate the iPod in the Sources pane on the left-hand side, then select the Music tab. Remove the tick from *Display album artwork on your iPod*, sync the iPod, reselect the option & sync again.

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