Chris C., the founder of ComputerAudiophile.com, has a great article about switching form iTunes to some other type of music server.
He has a detailed, and IMO very informative description of how iTunes handles metadata and why simply converting some files or adding existing files to a new music player might not give the same results for some albums as for others.
I know when I was toying with the idea of switching to Foobar, this problem kept me from wanting to proceed, as 1/3 to 1/2 of my titles lacked cover art, and I didn't want to retag them all. [now with JPlay, I'm set with good sound and itunes visuals

]
if you have any issues with tagging and itunes, check it out.
todd
http://www.computeraudiophile.com/content/457-guide-converting-itunes-dedicated-music-server/