[quote name='The Ebbtide']I can't recall if it fixed that issue, but there was a file called the Optional Media Update that allowed you to play AAC files, which is the usual file encoding that iPod and iTunes use. I'm fairly certain that it still won't let you play iTunes purchased songs for legal reasons.
Also, what's cool about the setup is that you can actually generate a 'playlist' while connected to the 360. If you go to your media settings or player on your Xbox 360, there's a way to select songs and organize them into a set list for it to play. You can actually take individual songs from your iPod and play them with this new playlist, but it self deletes as soon as you turn off the system or delete the iPod. I used to do that for bot battles in Perfect Dark Zero and Endurance Races during Forza 2.[/QUOTE]
Well all of my songs are in MP3, so I'm in the clear for that. And I have the OMU. And none of my songs are purchased through iTunes. Looks like I'm picking up an iPod Classic the next time it goes on sale, thanks Ebbtide.