Keeping track of missing files

I recently moved into my college dorm, and to help me out musically I got a 300GB Western Digital MyBook to keep all my tunes on. Unfortunately, I've had a couple problems with it since I've been using it, mainly when I sync up my iPod. Random songs will often come up missing in my library, and I was hoping there might be a way to easily keep track of or hunt these down, similar to the Show Duplicates feature. If not, there really should be because there's nothing quite as frustrating (at least, in iTunes) as thinking a song's playable and available to transfer only to find out that it's actually missing, and I have to go find it in the directory where all the other songs that it knows exist already have been and will always be.

I think I may have solved this issue by copying my Library files into a folder containing the Music folder on my external, just like how the file tree is setup on the internal drive, and then holding option when opening iTunes. I'm not positive that's the best solution, but it might just work.

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