ITunes Media Files can't be located (although they are there)

I have an odd problem with my iTues library. For some reason, most of the files (movies, music, and podcasts) can't be found. I then have to manually go and pick the locations (which isn't feasible since there are way too many... and it isn't even smart enough to find other titles on the same album after I picked one...). All the files are exactly in the folders they would be expected at though. It is really weird.
The only thing that is unusual about my setup is that I have my library on an external harddrive.
Oh, and all my album covers and other art I assigned manually is gone too.
How can I fix this either manually or by means of a third party product (it seems in general that there s a great need for a third party product to fix and edit iTunes libraries... I have also ended up with duplicate entries over time for some reason...).
Thanks for your help
Markus

What happens to me is that I load cd from my 250 cd player to my Itunes. When I click on it sometime thereafter, I am returned the message the the file can't be found.
This is constant. It's frustrating, because I have search for the file again. For those mix tapes without information, Track 01 and Track 02 etc., I have to figure out which one is missing or fill in the information over and over again.
Can anyone help. I'm tired of reloading the cds.

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