What seems to be such a simple task can be painstakingly grueling.
My mission: To sync Outlook with iCloud so my Outlook Calendar and Outlook Contacts would always be in sync WITHOUT having to connect the phone via iTunes every time I made a calendar change.
Software: Windows 7 and Microsoft Outlook 2010 running in Parallels 10 on Yosemite
The challenges: Too many to list, but the basics hurdles were once iCloud was installed the Outlook Calendar and Outlook Contacts were both moved to new files. That's fine with one major exception. When adding new appointments or contacts, they would go to the default calendar and default contacts which would not automatically sync with iCloud. The new appointments and new contacts had to be manually moved to the iCloud calendar and contacts in order to sync. Yes, manually. Another big hurdle for me was the fact that once all contacts were moved to the iCloud folder, searching for contacts within Outlook became a pain. Results were not returned as I typed. Also, my view in Outlook shows the To-Do Bar. After my calendar appts were moved to the iCloud calendar, the To-Do Bar was empty. Not cool. I attempted to sync to iTunes wirelessly. However, my install of Windows 7 is running in Parallels and I couldn't configure the network within the program to get an IP that's considered to be 'on the same network' for both devices.
The fix: After what seems like hours of research and testing, I came across a little jewel of a program called Sync for iCloud by CodeTwo This little program is a headache saver. It's free to use for 15 or 30 days, so I installed it. After getting it setup and being patient, it flawlessly synced my calendar and my contacts with iCloud. I used it in trial mode for about 3 days and made the purchase. It's been $20 well spent. Be patient after installing and setting up. It took a good 30 minutes to get things rolling between my devices and the cloud. I'm extremely happy to report that if I add an appt on any calendar of mine on my PC, my iPhone, or my iPad, they're all in sync within a few short minutes. Same with contacts. I can add one on my iPhone, and watch Outlook populate within just a minute or two. It's awesome!
Conclusion: Save yourself a ton of time and headache and install and buy Sync for iCloud.