I recall sitting in Building 117 (now named Studio H for some reason) in Redmond around 2005 or so (give or take a year) and suggesting to the Windows Mobile PIM group that they sync Hotmail, its calendar, and its contacts list over the air with Windows Mobile phones and Pocket PCs (over WiFi). My rationale was that ActiveSync was (and is) a total disaster and Microsoft needed to provide a simpler solution to its Windows Mobile customers. A few years later, hardware vendors or carriers decided not to bundle Microsoft Outlook with Windows Mobile smartphones. So, customers now had to buy Outlook if they did not already have a copy. I voiced my suggestion again. Both efforts were met essentially by silence.
According to LiveSide.net, a half decade later Microsoft is finally “almost” ready to provide over the air (OTA) syncing between Windows Live Calendar and Windows Mobile phones.
Of course, anyone who cares to do this (like me) already syncs their Windows Mobile phone using Google Sync (powered, ironically, by Microsoft Exchange ActiveSync). Google syncs email, contacts, and calendars very nicely, thank you. Too little, too late. Better luck next time.