Did anything happen the second time you hired Orris? If not its probably a bug and if you're on the PC you may have to reset the quest/set the flag to get the dialog option.
The thing is, I don't remember, I just loaded this save up after not playing for a while. I am on pc, maybe I'll reset the quest, what's setting the flag mean? I'm not on the game now, but there's an option to abandon the quest I'm guessing?