Hi guys,
After hours of troubleshooting I think I discovered an issue between OlympiaServer and the Latin1_General_CS_AI.
We created a new MSSQL 2016 database (COMPATIBILITY_LEVEL = 130) for Olympia server and we started getting errors about unknown column names. (EventId, EventUser, etc).
To make the story short, the only way we stopped having issues was if we recreate the database using the backwards compatible SQL_Latin1_General_CP1_CI_AS collation.
So for anyone out there having issues that will be something to try.
It is important to mention that Microsoft is pushing towards using the Windows collation (Latin1_GENERAL_CS_AI) for new databases. They will be using for a while the SQL collation for cloud services to avoid compatibility issues so on that part we are safe.