I don't have a Server instance to test with, so I can't recreate the problem.
Since you can easily use eventcreate, try 3 tests.
System
Local account that's in the Administrators group.
AD Account that's in the Administrators group.
In your local security policy, enable success and failure auditing for "Audit logon events".
Do any of the tests work? Check the tasks's history to see what events get generated.
Then check these event logs to see if there's anything different when a task doesn't get generated.
The normal System/Security/Application
Microsoft-Windows-TaskScheduler/Operational
There could be something in User Rights assignment that needs to be tweaked.