Sweet Mother of God. After losing all my hair, I finally found a solution from digging around at http://answers.microsoft.com/en-us/office/forum/office_2013_release-outlook/outl ook-2013-keeps-disabling-icloud-add-in/5….
The solution:
1) Run Outlook AS ADMINISTRATOR.
2) Go to File > Options > Add-ins.
3) Click GO next to COM Add-ins.
4) Select the iCloud Outlook Addin and REMOVE it.
5) Close and restart Outlook AS ADMINISTRATOR.
6) Go back to File > Options > Add-ins.
7) Click GO next the COM Add-ins.
8) Click ADD and find APLZOD32.DLL on your machine.
9) Close and restart Outlook normally (NOT as administrator.)
Now my calendar is syncing properly.
Apple, are you reading this? Shouldn't your iCloud for Windows installer deal with this sort of issue??