John can't get his Outlook calendar to sync. Leo says syncing is a dark art. Issues in sync include data duplication, and multiple calendar users. His issue is with Outlook and Google Calendar.
Leo says that Outlook is a poorly written Calendar. Leo advises getting rid of it altogether and relying solely on Google Calendar. It'll work with anything, any platform (except Outlook, obviously), and it'll sync. He should make sure Outlook email and announcements are set in his settings. He should have no issues once he goes to Google exclusively.