Why does iTunes keep messing up the album covers?

in Genius Bar edited January 2014
Whenever I update my iPod I lose all of the album covers of any old songs that were on it before the update. Only the new albums that I just attached art to will show up. Why is that?

Does it have anything to do with me deleting everything from my library and re-importing my music folder each time I update my iPod? I do that because I'm constantly adding new songs and CDs and deleting old ones I don't like anymore, and instead of having to worry about deleting them individually from the library I simply delete everything at once and then re-import my folder.
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