I will admit that I'm not always the most organized gal. My dorm room floor is currently covered with a nice layer of black underwear, CTA cards and old New Yorkers (magazines, not Manhattanites).
But I am obsessive about the organization of my iTunes. Every song must be labeled properly. The album listed must always be the original CD- never a "Greatest Hits" or "Best Of" album. I've even taken to naming my genres very specifically in order to be a hipster/jerk. Think "surf & garage revival" and "post-modern art rock".
Helping me in this task is spiffy free software called TuneUp. It helps you find missing album artwork and label all of those songs named things like "Track 03". I give it four out of five stars. Download it here.