Outlook calendar updates not updating
If you want appointments added to the i Cloud calendar, you'll need to either move (or copy) the appointments to the i Cloud calendar or create them directly in the i Cloud Calendar folder. While you can't configure Outlook to use the i Cloud1 data file as your default (i Cloud2 can be set as default, with limitations), you can configure Outlook to startup in the i Cloud Calendar folder.
Don't use i Cloud calendar, contact, or tasks sync for Exchange, Gmail, or Hotmail accounts.
If the calendar view is set on High details, check your all days events for end dates.
This happens because i Cloud doesn't see your account as the meeting owner.
Open any event that has No end date and set an end date.
I recommend using 10 events for yearly events and 1 year for more frequent events.
Outlook Today gets appointments and tasks from your default Calendar.
If you use i Cloud 2, you can set the i Cloud data file as the default, however, this will not work if you use an IMAP account. Although you can't set the i Cloud calendar to be the default, you can configure Outlook to display the i Cloud calendar when Outlook is opened the first time.