What did you use before you moved to Windows Live?
I don't think Windows calendar is supported. I know Outlook 2007 is. Download and install DM 5.0. If Windows calendar is included, it would be using that DM version most likely.
Here is a link from the Microsoft Support Forum concerning this issue. Blackberry sync for calendar and contacts - Windows Live Help
ALso using the SEARCH function, I found this: Contact syncronization options?
It appears Windows Calendar and Mail are not part of Windows 7 either.