IPod Touch 64GB keeps losing artwork/artwork in iTunes not showing up on corresponding albums

after installing an update on my iPod Touch I noticed almost all the album artwork was erased. I'll just list the progression of events in order they've occured:
Install OS update on iPod Touch, almost all artwork is erased.
Re-add several of the albums that were missing artwork, artwork shows up fine.
Install second OS update that comes out.
Artwork is once again missing. Some albums I 'fixed' remained unchanged but all the files that did get the artwork erased were songs that had had it erased the first time.
Re-add a few albums that were effected, but some in the middle of it, iTunes crashes and things are messed up again.
I've tried all the basic fixes that people suggest for this kind of thing. Nothing seems to work. And it seems that whenever a particular album's artwork is lost on the iPod, it's lost in iTunes as well and neeeds to be downloaded again.
It's getting very tiring and I need to find a way to fix this so I'm not constantly worrying about re-adding songs and artwork and all that.

I had the same problem with artwork dissapearing, after I upgraded to ios5.
Never found a solution other then re-uploading the songs & artwork. Very time-consuming.
Sorry to hear that it's still happening - I'm really not looking forward to going through that again.

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IPod Touch 64GB keeps losing artwork/artwork in iTunes not showing up on corresponding albums

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