Artwork shows on some, not on others

I am a new Ipod user, but am by no means computer illiterate. This program may cause me to reconsider. After losing 800 songs to I tunes, I am in the process of installing all 5000, ten at a time to see which ones go in and don't.... Not the point.
I have been playing with downloading album artwork from Amazon, and adding it to my file info. Now I have noticed that not all of it transferred. I tried the delete all album artwork, then reattching all album artwork from the sync page, but no dice.
Any Ipod/Itunes genius able to help me?
Thanks

Thanks for the tip. I have tried the auto-import of the artwork, but have had little (though some) success.
As far as the losing of the songs goes, I have been collecting for years, and have aquired from many different sources. All are saved as *.mp3. I tried to take the directory on my desktop that held my tunes, open it, select all, and drag and drop into I-tunes. Worked, but not all of them went, and when you have a bunch of tunes, it is difficult to determine which did and didn't. Now, I am installing them by placing my backup cd's (mp3) in, adding them to a folder, and installing the new songs 10 at a time. That way, I can catch what is/isn't making it, then force them in by right click, open with ITunes.
Pain in the butt, but is working. (Though VERY slowly) any suggestions to speed it up?

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