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There is so much that's right about Xbox Live that it becomes painfully obvious where Microsoft dropped the ball with online support. It is as if the person with the vision for Xbox Live won the lottery and quit his job before the entire solution was complete.
Since Xbox Live provides a comprehensive gaming environment where voice chat, instant messaging, and gamer achievements all come together with downloadable trailers and demos, I'm certain that more than 75% of Xbox 360 will take advantage of the non-multiplayer-gaming elements of Xbox Live.
Mistake #2: No MSN Music
The distribution model for Xbox Live has the potential to rival iTunes. Microsoft already has a complete micro-transaction system in place for buying Xbox Live Arcade titles or various skins and upgrades for games. Microsoft already happens to have access to a rich library of music through MSN Music. Since the Xbox 360 is already engineering for DRM, it would have been easy for Microsoft to introduce MSN Music capabilities to the Xbox 360.
I'm as much of a fan of DRM as everyone else (which is to say I don't like it), but with Microsoft already charging gamers for Xbox Live Gold support, it would have been possible for Microsoft to offer discount service "bundles" allowing you to buy unlimited subscriptions to the MSN Music library at rates less than you would have to pay for Napster or Rhapsody. Gamers would have had an opportunity to get music cheaper and add one extra weapon in the console battle against Sony.
This was a no-brainer. Think about it, buy music using your Xbox 360 and Xbox Live and transfer it to your "Plays for Sure" Windows Media Player. Integrating MSN Music with the Xbox 360 would have helped Microsoft compete with Apple.
The technical infrastructure is there.