Kept on having issues with Outlook connector no syncing my Windows Live Calendars.
It was pointed out to me to check my Send/Receive groups, and sure enough mine had some odd settings.  I have a really unique set up for them, and forgot that i had turned some of them off a while ago. Turned them back on, and now they work fine.

Too bad i can’t see my events from WLC on my Upcoming events pane. Perhaps in W4.