Anyone ever have this happen?

So my iTunes library is on an external hard drive and I thought my iPod was not importing the artwork for my songs, even though it was visible in iTunes. Anyhow, it turns out that the first 2-3 songs in every one of my album folders did not have the artwork on the files themselves (like when you look at the icons, it looked like a generic iTunes file) but the others did. if I did apple-I in the main window though, all the tracks showed the artwork
any idea how my files may have gotten messed up? The iPod IS importing the art, but obviously only for the songs that have it on the actual file. ALL of the files had art before, but now the first 2-3 songs on EVERY album has it missing.

I noticed the problem started happening when I accidentally plugged in my iPod without having the external hard drive turned on (I have a stereo system in my room and don't use my computer to listen to music, so the only time I go into iTunes is to load the iPod.
Could that have caused those files to get messed up?
I notice if you remove the album artwork folder iTunes creates a new one. Maybe that folder got corrupted somehow?

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