You could sign up for Google music beta! (google.com/music). It can sync your iTunes collection to listen on any Android device. I'm using it on both my phone and my Xoom and it works great. You can even save certain playlists/songs to the device so they are always available. Currently you can sync up to 20,000 songs.

Google music does not, however, work with older iTunes music that was encrypted. You can either pay Apple to get the unencrypted versions, or burn those tracks to a CD and then re-rip them as MP3 files.