IPod Classic will not update certain playlists

I have a 120GB iPod Classic running software 2.0.1, and I cannot get it to update some playlists. Some will have a different album artwork than in iTunes, and the couple that I really care about are in reverse order.
I tried creating new playlists of the same albums with slightly different names, but they still show up in reverse order on the iPod, which doesn't work so well for a story.
Last nigth I got so frustrated that I restored my iPod to try to get it to work, but still the same playlists are showing up in reverse order.
I have tried restarting my iPod, reseting it, restoring it. I have even run diskwarrior on my iPod, and have tried trashing the com.apple.iPod.plist, to no avail.
Does anyone have any ideas, or am I SOL?

Update!
This is what I did to fix both the skipping songs problem and the iPod verifying forever & not able to restore problem (because of iTunes 9):
a) I used Disk Utility to reformat my iPod while in Disk Mode using the instructions here:
http://support.apple.com/kb/HT1363?viewlocale=en_US
and here:
http://www.methodshop.com/gadgets/ipodsupport/erase/index.shtml#backup
b) Do not unplug your iPod after reformatting (mine showed up as a firewire disk) - simply launch iTunes ( I went back to 8.2) and follow the Restore instructions here:
http://support.apple.com/kb/HT1339
iPod is recognized, syncs and doesn't skip songs anymore after that miserable experience with iTunes 9!!!

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IPod Classic will not update certain playlists

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