Brandon is struggling with keeping Outlook in sync between two machines (via Scoble).
Many of you know this is something I've struggled mightily with in the past and I eventually found a solution - namely, running SBS2003 on a Virtual Server. I've written a bit in the past how well this works for me, but I have to agree with Brandon here - why does it have to be so difficult?
As I said in that post:
This begs the question though - why doesn't Outlook support this sort of stuff out of the box?
I can't imagine I'm the only one with multiple machines who wants access to all of my information from anywhere. I don't need all the enterprise features of Exchange (nor do I want the overhead). This solution would work equally well if it were just a lightweight service running on my primary desktop, allowing another Outlook installation to connect to a 'master' Outlook server. Outlook Web Access would be supported as well, with the obvious IIS prerequisite.
It seems that, if you want people to start using more than one computer (which, presumably, Microsoft wants), they would want to make it easy to do so. Keeping things synchronized is an important step towards making that process easier. This was part of the reason I was really looking forward to WinFS - the synchronization features.
Of course, I doubt we will ever actually see this, especially now that MSN launched Outlook Live.