This may be old news to some of you, but I just heard it today so I'm sharing:
lifted from here...
“To attract current iPod users Microsoft is going to let you download for free any songs you've already bought from the iTunes Music Store. They'll actually scan iTunes for purchased tracks and then automatically add those to your account. Microsoft will still have to pay the rights-holders for the songs, but they believe it'll be worth it to acquire converts to their new player.”
Damn, I think that's kinda cool.