The problem being addressed here is that the iCloud add-in gets disabled each time outlook is closed and restarted.  This is only a problem for people who want to have their iCloud synchronized with their Outlook.  This solution should be applicable to Win 7 and 8.1 and Outlook 2010 and 2013.
  1. Start Menu > regedit
  2. Select : Computer/HKEY_CURRENT_USER/SOFTWARE/MICROSOFT/OFFICE/OUTLOOK/ADDINS - Apple.DAV.Addin -
  3. On the right, double-click on LoadBehavior and check the value: if it say 0, set it to 3.