Apple really need to fix that cockup that is Sound Check. It just doesn't work. Sometimes it helps, sometimes it makes things worse. It goes too far, so rather than ending up with tracks the same volume you just get loud songs quiet and quiet songs loud, with a few that just don't change. They really ought to start adjusting by maximum volume, rather than average.
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Itunes is just buggy on my computer. It always deletes my music.
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If music is in your iTunes Library folder, then it will ask you if you want to delete the file when you remove it from your playlist. Just put it in another folder, that's what I do.