Ah, I think you’re right. I knew another pair of eyeballs would be able to spot a difference. I’m actually running iTunes on OS X — but since it’s not case-sensitive either, it would have the same problems.
I think I need to just fix the file path in my iTunes library but I’m not sure how to do that, short of deleting and re-importing the songs.
Will try later and let you know if that fixes things. Thanks!