(Right now, you basically have to download the music once, and then sync it across many devices on your own, primarily through USB.)
This is a no brainer for Apple. They want as few restrictions as possible on downloaded music because it’s better for consumers, and therefore better for its stores. Meanwhile, record labels want restrictions because, well, they’re record labels.
Apple’s music store has 70%+ marketshare and Steve Jobs knows how to drive a hard bargain. But Apple does need the labels as much as the labels need Apple. Bloomberg sources say there might be an agreement by the middle of this year. We’ll see.