Get the FUCK off of Itunes, it's a music collectors worst enemy. I use MediaMonkey, but there are tons of alternate programs that run much better then itunes could dream of- just less pretty. I would take all your music and make sure it's in your hard drive, delete Itunes, and get a new music manager. If Itunes hasn't screwed you yet your bound to get it. Also I would consider getting some back-up for all your music and not just putting it in your hard drive, maybe you can plug the hard drive into another computer and keep all your files in that computers internal hard drive as backup. Maybe just .zip everything and send it to friends, but external drives lose information more often then internal ones do. Keeping things internally takes up too much space though, so meh.
Also try exporting your palylist or instead of editing id3 tags in itunes editing the actual files themselves. Mediamonkey has automatic id3 tagging. =))
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