Just plain CRAZY iTunes behavior

Question

This is a request for insight as to what might be going on. I've searched & searched for a solution but don't expect one until Apple provides some sort of library/database repair function.
-> After defragmenting the hard drive with my iTunes folder on it, iTunes thinks that roughly 20% of my music is linked to random files on the startup drive (different from the music folder drive). Crazy random file types are listed in the "Where" section of the "Summary" tab in the song's info. tiff, htm, do, iges, you name it.
And, of course, now iTunes dutifully gives me hundreds of errors (thankfully grouped into one dialog box) every time I synch an iPod, alerting me that it won't copy the odd files to my iPod because the iPod can't play iges and htm files.
I rebuilt the current library from scratch about a month ago and have recently re-imported the whole music folder (by dropping the iTunes music folder from the Finder onto the iTunes application window) to retrieve all the real music files that iTunes miss-linked. This resulted in about 1000 "duplicate" files but at least the music is in there for iPod use. Now I'm going through manually and deleting the miss-linked files after transferring my star ratings. *good times*
-> So there it is. Any ideas as to what's behind this craziness?
-> Any other votes for an Apple iTunes database repair tool?
-> And is there anyone else out there who shuns iPhoto because of what would happen if it's single gigantic photo database has even half the problems that the little iTunes library has?

Answer 1

I notice that too on my Macbook Pro.
I think that is some kind of issue, because I didn't find any option for that.