Looks like Chris Pirillo has found more things to dislike in the new Outlook than things to like.
I think the problem is simple - developers don't know when to stop, and management doesn't want them to stop. Office is a huge chunk of MS' revenues, and there's a corporate need to drive upgrades. That's why management wants churn. However, take a look at what is, for the most part, a mail client. Is there really that much more it needs to do? Is the complexity inherent in making it a combined PIM, email client, and RSS reader worth it?
Based on what most users of Outlook seem to say, I don't think so. It's too big, too bloated, and too unfocused on any of the things it does. What I think MS really needs is 3 smaller, lighter tools here that can communicate in some fashion. That's not going to happen though - instead, the suckage will just increase.