I have a desktop and two laptops all running WIN 10 with Outlook 2016 and ICLOUD. What I have discovered is that ICLOUD must be installed on OUTLOOK 2013 and must be Revision 4.1. Once installed Outlook 2013 can be removed and 2016 installed. Outlook 2016 will get the profile created in Outlook 2013 and enable ICLOUD. Do not allow ICLOUD version 5 to install as it will kill the operations in 2016. ICLOUD version 4.1 is available on a couple of download sites, but be cautious of extra programs being installed. Apple does not seem to make version 4.1 available anywhere that I can find. I subscribe to Office 365 and therefore have the ability to install either 2013 or 2016 versions or both under my contract.
In the case of my desktop it was not a major problem since I had ICLOUD 4.1 on Outlook 2013 which was later updated to 2016. I did not allow ICLOUD 5 to install as I heard about all the problems with 2016 & Ver. 5. This brought me to the conclusion that ICLOUD and Outlook could communicate properly.
I recently setup a new laptop and installed Outlook 2013 with ICLOUD 4.1. I uninstalled Outlook 2013 and installed Outlook 2016. All is well with the system.
Through trial and error I have found that if you have Outlook 2016 and/or ICLOUD 5 installed, you must remove completely with a cleaner program as both leave residual files and register entries which will prevent any clean installs of subsequent Outlook or ICLOUD.