Is there a setting that would show also 'check out' operations in file history:
As you can see it only shows state transitions and check in operations, but never check out.
That would be a nice option but I don't think it is currently possible. I found this enhancement request:
SPR 529675 Enhancement : Add 'checked out' information to history listing ( so that it can be used as a event for comparison as well)
Retrieving data ...