Hi Bill_H,
You can try to resolve these issues after review the below articles:
• Rebuild the Outlook for Mac 2011 database: http://support.microsoft.com/kb/2360509
• How to sync calendars in Outlook for Mac 2011: http://support.microsoft.com/kb/2452489
• In Outlook for Mac 2011, an additional shared calendar does not open: http://support.microsoft.com/kb/2743766
• Share your Office 365 calendar: http://office.microsoft.com/en-us/outlook-help/share-or-publish-your-calendar-1-05-RZ103433663.aspx?section=2
Thanks,
Shyamal