One of my big complaints about the iPhone and then MobileMe was that Windows/Outlook syncing was horrifically bad and it was painfully clear that the Walt Mossberg/David Pogues of the world had never even tested these products together, not even once. Apparently, neither had Apple. Yesterday, almost exactly six months after it started charging customers $99 a year for MobileMe, Apple finally fixed the service so that it actually works on Windows. Yes, seriously.
We've recently improved the performance of MobileMe syncing with Microsoft Outlook on Windows. Contacts and calendars automatically sync whenever a change is made in Outlook, and likewise when a change is made on the web or from another device. To take advantage of this improvement make sure you're using iTunes 8.0.2 and MobileMe Control Panel 1.3 and that you have "sync" set to occur "automatically" in the Control Panel.
So, my advice hasn't changed. Sure, use an iPhone. It's wonderful. But forget about the insanity of MobileMe and its yearly charge.
Thanks to Nick R. for the tip.