Using older versions of Outlook for Mac in business environments
I had also the issue with getting stuck on Sync Pending right after a few minutes of (re)starting Outlook, that I had to work with the Windows Outlook out of a VM.
Following approach seems to have solved the issue - at least for me:
I deleted/removed my Exchange account from Outlook completely, restarted Outlook, adding the Exchange account again.
Since then no "stuck on sync" issue anymore.
Don't know if it maybe was caused by my move from Outlook 2011 to Outlook 15.3 (the account with settings were moved automatically).
But I had the issue with version 15.3 and the current 15.6.
At least my Outlook is working now - maybe this helps one or the other as well.
Kai