How to deal with it in a timely manner transfering to itunes from a external hard drive collection which is a true mess. Good mp3 files just unorganized. Something on the order of 100 gb. Multiple file names, running song lists, as well as duplicates. Help. My itunes account lives on a HP windows 8 machine (which my wife and I hate). I have a ipod 64 gb, and a ipad 64gb, and not quite ready to purchase a rMBP, or a MBA just yet.