God, what a nightmare.
Not only does it look like you have to jump through hoops to get things running at all, but... is anyone else offended by the wannabe-trendy images that are displayed all over the place during the process? (And I assume more of these pop up throughout using the Zune and its marketplace).
Man -- they are just trying soooo hard to be "hip and cool," but it just gives off the opposite vibe. And it seems to be trying so hard to target such a specific group of music listeners too. The beautiful thing about the iPod is that it doesn't really discriminate with musical tastes. Whether you love hip hop, rock, country, classical, jazz, alternative, rap, world music, oldies, or whatever -- ALL genres and types of listeners are welcome with the iPod (reinforced by the variety of different ads they've had). But I feel like a large portion of music listeners would be put off by the Zune, which seems to be only targeting teens.
It's quite possible teens might fall for this device and choose it just to "be different." And I'm sure M$ will throw tons of money towards marketing it and it will stay around for a while. But it's NEVER going to touch iPod sales with the way they do everything in their power to limit themselves.