Hey everyone,
Just wanted to let you know that the following workaround worked for me.
I still have iCloud 4.x installed. As soon as I saw the Outlook 2016 warning in Version 5, I made sure not to install it.
Like many of you, the latest Windows update broke it, despite me not using 5.0.
No Calendars; No Contacts. Brutal!
Yet I was now able to fix it.
Navigate to C:\Program Files (x86)\Common Files\Apple\Internet Services
Right click on iCloud.exe, and ensure it's running in Windows 8 Compatibility mode.
I used Task Manager to kill the current iCloud process, and then re-ran it by clicking on the .exe file.
I unchecked the Outlook Sync option in the iCloud Panel, then I re-checked it.
Bingo!
Now I see my 1,900 contacts as well as my two iCloud calendars. Two reminders just went off two. I was really so happy to hear the reminder ding, even though it's after 2:00am and it woke up my girlfriend!
I am a newcomer to the Apple ecosystem, and I have to say I am really disappointed. I really thought Apple's products were supposed to "just work", but really - they never do lately. So many issues and annoyances with every device.
I am still trying to figure out if Apple was always like this, and people were just caught in Job's distortion field, or if Apple DID release near-perfect software and hardware in the past, and all these incessant problems are relatively recent.
I still can't get a definitive answer. It's a shame. Apple makes incredible devices; amazing hardware... but my new Apple TV.... my Watch... iPhone.... this Retina Macbook... each one has had so many annoyances. It seems like I am always waiting for the next iOS or OS X update for one reason or another.
Well, I do hope the workaround works for you.
And I did leave feedback for Apple, too.
Thanks!