No-one PM'd me. So I think this thread is dead. I've been dealing with lots of Mac users post-migration. My advice is this (seems to mostly work)
1) Update to Yosemite
2) Perform all software updates
3) Check and apply all Office 2011 Updates (Several times, reboot machine after each update)
4) Install New Outlook
5) Check and apply for New Outlook Updates (Several times, reboot machine after each update)
6) Now try
7) Remove any accounts in New Outlook and Re-add if there are sync problems
This post may have been for an older version (15.6), as the newer version (15.8.x) seems to work a lot better. That may also explain the absence of a PM. Not sure.