One of the more irksome qualities about the Outlook Connector was the lack of Calendar synchronization, particularly with the new Windows Live Calendar. If you were an MSN subscriber it would work, but if you had just a Hotmail (or Windows Live) account it wouldn’t. This also applied even if you had purchased the additional features of Hotmail Plus.
According to LiveSide there is a new Outlook Connector currently in internal Microsoft testing that reportedly allows synchronization with Windows Live Calendar. Hopefully the new version includes some other improvements and bug fixes (particularly on speed and the fact that Outlook Connector periodically looses my stored passwords).