Region based market segmentation is a whole different problem. How about just being able to sell digital music in Latmonroviastan in the first place? It was a good two years from the opening of the iTunes music store in the US before the iTunes music store in Canada opened - and that's Canada! We're practically the 51st state! Last I checked, none of the really cool music services like rdio or pandora were available outside US territory.

Update: I was wrong. Rdio made it here. Yay!