Aesthetics. And that, sadly, is why the Zune can never win.
No news about whether this version will let you play songs you got for, uh, “free” (and come on, what’s the point of owning an mp3 player if you can’t control which songs you can play?). Price doesn’t seem that different from the iPhone ($219 for a 16 gig Zune vs $199 for iphone with similar specs). So it’s down to aesthetics:
Compare with the iPhone:
The Zune’s design is so overdone it’s hard to tell if it was imitating the Nokia 6300 or the iPhone. It’s angular design and austere logo may lend it an air of ‘business’ but the blocky all-caps sans-serif interface screams arrogant hipster. Which means? HD or no, just about everything from package design on down to apps and appearance will signal square.