Can't Sync Outlook 2013

Question

On my work PC, I was recently upgraded to Office 2013 from Office 2010. iCloud had been happily syncing my contacts, calendars, reminders, etc., with Outlook before the upgrade and continued to do so afterwards. However, I've had the issues other have also reported with Photostream not working, so when iCloud Control Panel 4.0 came out, I asked my IT administrator to give me the update in hopes that it would solve that issue (it didn't). Once that was installed, iCloud complained that there were two versions of Outlook installed and we discovered Outlook 2010 hadn't been removed. We removed it. After removing the old version of Outlook, iCloud seems to think there is no version of Outlook installed -- in lieu of a check box to sync my contacts, etc., iCloud says "You can access Mail, Contacts, Calendar, and Reminders at iCloud.com."
Is there any way to help iCloud see my Outlook installation again? I've tried signing in and out, I've tried deleting the Apple folder under AppData/Roaming and I've even tried removing the Outlook folder under AppData as well. No luck.
Thanks,
Tim

Answer 1

So I was having this issue and I don't have a long-term fix, but I feel as though my short-term fix may help ease some frustrations. I don't work for microsoft, but here's what I did:
Background:
My situation was that I tried to import my gmail contacts but found that many were missing in my address book. My contacts were however synced to my outlook.com web account, so I tried using those gmail steps with outlook. I know that other people were having
issues with hotmail, of which I can't help because I don't have an account, but if you can find a way to import it into your outlook.com account, this is what you do next:
To sync your outlook.com contacts with your outlook 2013 program, you can easily export your contacts through outlook.com: 
Outlook --> People --> Manage --> Export
The file should start downloading, and will be named WLMContacts.csv. Then click the below link and follow the steps below starting from "Import your Google Gmail contacts into Outlook" (it's about halfway down, after step 7 of the "Export your
Google Gmail contacts to a file").
http://office.microsoft.com/en-us/outlook-help/import-google-gmail-contacts-into-outlook-HA104035588.aspx?CTT=5&origin=HA102919678
After these steps, your outlook should pop up with a progress bar screen and start syncing the contacts. To check if it worked, try a contact that you know didn't appear in your Outlook program before.
Best of luck, and I really hope this helps until Microsoft fixes the issue!
-Winnie