Perhaps the real crown jewel of Apple software, iTunes is not just a music player- it’s a portal to Apple’s music and video store and the gateway to the iPod and iPhone.
Dropping iTunes is really tricky, especially if like me you have an iPhone. For the time being I sync my iPhone to iTunes in Windows.
I managed to move my music out, although the great cover art Apple ‘provides’ isn’t actually in the files. There are disk space reasons for not embedding artwork in every file and this seems to be common among all the great music player software.
As a music player, iTunes is a pretty smooth and nice. But it epitomizes Apple locking you in. Yes, it’s available on Windows. No, that does not make it any better.
Migration Score
AWFUL
Migration Options
The absolute lock-in to iTunes caused by Apple's DRM that's embedded in much of what they sell in the iTunes Store made switching here a nightmare. You can use Noteburner to convert your locked music to a format like MP3. Essentially this is legal because Noteburner is a fake cd burner that iTunes burns to and then somehow copies over metadata into the files it generates. There was enough "slippage" in the conversion that i had to go back through and edit many files' meta data (titles, etc.). The built-in tools for both the following players made that pretty easy.
Any video you've purchased is nothing but trouble, and I've purchased a lot. The only thing that can be done is to play the video in a player on an authorized computer and do a screen capture of it. Three problems: the quality of these will be tweaked by you so it won't be as good, the audio and video may get out of sync, and this has to be done real time- that is you have to play all of your videos all the way through to capture them and that doesn't include saving the capture in a usable movie file. To be blunt, it's not worth it. It's a definite warning about purchasing anything that is not in an open format.
Rhythmbox
Ubuntu defaults to Rhythmbox and it's proven to be a great media player for me.
Banshee
Another great music player, though not the default for Ubuntu. It works well.
Hulu
For videos- start watching online instead of buying. Free and you can do so on any platform that has the free Flash Player.