Songs "can't be found" in iTunes

About 7 months ago, I spent a considerable amount of time putting a large collection of CDs into iTunes after purchasing an iPod classic. Because I thought the files would take too much space for my hard disk, I bought an external hard drive. I thought I had successfully set this up as the place for all my iTunes files. Sometime since then, this setting was lost in iTunes, and Edit > Preferences > Advanced > iTunes Music folder location reverted to a My Music folder on my C drive. I have now copied all the files from there to the external drvie and have attempted to change the iTunes Music folder location to match. So my .m4a files are now in folders like K:\iTunes\ABBA\ABBA_ The Definitive Collection, and the Musci folder location is K:\iTunes
But when I choose an Artist and Album in iTunes, and then click on the first track to play it, in about 75% of cases I get a dialog telling me that the track cannot be played because the original file cannot be found. If I accept the offer to locate it, I can always do so by choosing folder names to match the Artist and Album name, and then choosing the right track. And iTunes does remember the track location after that. But with about 500 albums, you can imagine how much I wish to do this in order to relocate about 8,000 individual tracks, one by one (locating one track on an album does not locate any of the others, as far as I can tell). Is there anything I can do to automate this process, and any explanation for what's gone wrong? If I connect my iPod to add recently purchased tracks to it, what happens to all the tracks that "can't be found"?
I'm currently using iTunes 8.0.2.20

You get exclamation marks or dead tracks because iTunes can’t find the file. This can happen for a number of reasons:
The song file or a folder in its path was renamed
The song file or the folder it is in has been moved
The song file has been deleted
The device containing the song files e.g. external drive is not accessible or the drive letter has changed.
A changed drive letter is a common cause of the problem if you are using an external drive, but that should affect all tracks.
Assuming you are not changing things yourself, to you have any other music player software that is looking at you music folders and possibly doing some organising?
If the music is in your iTunes folder, there have been reports of iTunes getting in a muddle if it is set to keep your iTunes Music folder organised. You could try turning it off.
A simple way to get everything back is to add your itunes Music folder with File>>Add folder to library. This adds all missing tracks, but leaves the dead tracks which have to be removed in another way.
Watch out if your music is not in the iTunes folder - you need to make sure that Copy to iTunes Music folder when adding to library is not checked if you don't want the tracks to be copied.

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