Adding to my list of things that I wish I could do in iTunes:
I wish that it could synchronize my song ratings across authorized machines. That way, when I follow Merlin Mann’s most excellent advice re: smart playlists that incorporate ratings, I wouldn’t have to duplicate my efforts as much.
I already use the “music only” trick to share songs and nothing else across our company network. If you keep company information in audio form on your hard drive and use iTunes to share your playlists, you should really, really make sure that you’re not sharing more than you intend. You know the difference between a song and a client call, but software doesn’t.