Zune Thoughts: Dave Winer Cronicles Struggle with Zune Setup

I've been watching, a bit flabbergasted, at how much trouble Dave Winer is having getting his Zune set up and ready go be used. I'm well aware of the many issues related to the Zune software and setup process, but Dave's inability to get the Zune working is, well, stunning. I sent him an email to offer my help, but he hasn't responded in several days so I suppose that means he's not interested in my help (or maybe he's just slow to respond to email like I am sometimes due to volume). So I figured I'd help him out in public. To properly de-construct this issue, you'll need to read part one, part two, and part three. Got it? Good.

Now Dave admits that some of the problems he's having might be because he's using Parallels on a Mac, but some of the issues he's having seem truly bizarre. The Zune says it's synchronizing, but when he looks at the device, there's nothing on it? I've never heard of that one before. I think many of the problems are between the chair and the keyboard/mouse - i.e., Dave himself. There are clearly some lessons here for Microsoft's Zune user interface design team - and I'd never argue that the Zune desktop software is elegant or particularly well-designed - but by the same token I think as a Mac/iPod user Dave probably has pre-conceived notions about where to look and what to do with the Zune.