Outlook and iCloud won't sync since Windows 8.1 upgrade

Question

So I've finally figured out my problem, but have no solution. The problem is that ever since I upgraded to Windows 8.1, Outlook "forgets" that the iCloud add-in is enabled. Every time I start Outlook, I have to manually go into options and re-enable the add-in. After that, syncing calendars and contacts to iCloud and my iPhone works just fine. In order to fix this, I figured out that I can set Outlook to run as an administrator. Works perfectly, as in now having the add-in enabled automatically. I thought this was the end of my troubles, but now Outlook no longer syncs with iCloud. Tried everything, and it just won't.I read on another thread that Outlook won't sync when you run it as an administrator. And sure enough, switching back to NOT running it as an administrator fixed the problem, in that it now syncs again. However, I'm stuck with re-enabling the add-in every time I start Outlook. Is there no other way to do this?

Answer 1

I don't use playlists. Maybe as a workaround you could try music software other than Windows Media Player, like Media Monkey
http://www.mediamonkey.com/
And see if you have better luck.
The free version of Mediamonkey should  do playlists for you; what you get with the Gold (paid) version, mostly, is an mp3 ripper, but you can also install an mp3 ripper without buying it.