Resolved: Oulook being stuck on Something is wrong with one of your data files...
I have come accross this error a lot:
something is wrong with one of your data files
But I have never experienced it persisting even after I had removed all profiles and clearing out %UserProfile%\AppData\Local\Microsoft\Outlook. I even repaired and then re-installed Office 365 - the error just kept showing up.
Turns out Oulook stores a registry key whenever it runs into that error and none of the above steps actually clears it out.
If you run into this error even after running through all the normal troubleshooting steps open regedit and go to:
Computer\HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Outlook\PST
Here you will find a key called promptrepair - set it to 0 or remove it and Outlook will start normally again.