I am so aggravated by my iTunes!
I have a bunch of music that I've purchased from Amazon, and I have to keep reloading it to iTunes because it will conveniently "forget" where the file is and refuse to play or upload when I'm making an update.
It also doesn't like my phone, an HTC EVO, much LOL!!!
I don't like to purchase music from iTunes, because I can't share it with my family. Amazon let's us share. Of course, they can't seem to keep their songs from Amazon on their iTunes either.