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iTunes sucks for a variety of reasons. It is closed source, slow, bloated, and the navigation paradigm makes absolutely no sense unless either you listen to music like a 15 year old girl (changing tracks every minute to keep the dance party going), or (certainly not mutually exclusive) your library consists of mostly single tracks as opposed to full albums. Songbird (admittedly I haven't tried it in about 6 months-- correct me if things have changed) suffers from the same problems, except at least its open.
I was satisfied with Amarok 1.4 for a long time until version 2 came out and the bloat prompted me to look for something else. Of course, I could have kept using the old version, but I quickly found Quod Libet which, in album view (http://img132.yfrog.com/img132/1773/screenshotmwp.png) is the best player I've ever used. Also the plugin framework is awesome and its the first open source app on my desktop I've ever actually modified, despite years of programming background. Edited 2009-07-25 22:38 UTC
On Linux I prefer Banshee or Rhythmbox. IIRC, iTunes copied the browser view from them. Don't have my own iPod yet. Might just get an old iPod mini and upgrade the HDD to an SSD; the nano is too small, and the Classic is too big for me.