personally i dont find itunes that bad, but to each there own. but i do like mediago alot better then itunes, it has lots of features, creating/syncing playlists, syncing music, videos, and pictures.
it also has a store built in, but its mostly for the PSP, and movies/tv shows, and podcasts, no music content at all.
i find the UI very clean and usable, it also has a compact mode, where it stays in front of all your open windows, but in a small bar at the bottom of the screen, giving you access to music controls without leaving your current window.
you can find it here: Download - Media Go - Sony Network Entertainment