So my wife has spent about a week with Outlook (2003) now. Her comment?
They must have spent a lot of quality time with the Ugly Stick
Now, having looked at the video of the new Office 12 - sorry Scoble, but it's not an improvement - in fact, my wife's comments when looking at the new Office 12 were, umm, probably not printable.
Some context - she's new to Office, and the tools she's been using are whatever Sun ships on their Solaris boxes. When you lose a usability race with Unix developers, it's generally a bad sign. There's a ton of wasted space in the UI, simple stuff like "how can I get myself included/not included in a reply to all" - it's hard to find. I last looked at Outlook seriously 5 years ago, and hated it. A lot. This week's experience hasn't made me want to look again.