The mission was a disaster on all scales. Oliver didn't like going undercover, but that was the assignment he received because he was the youngest member in the unit and had the traits most fitting for the job at House Moore.
Noble houses take many precautions when hiring servants, one of which is hiring young people from humble backgrounds who can be easily verified. Another method is hiring orphans who have no one in the world to be attached to. One of the most common methods is hiring the children of their current servants, which is the most surefire way to gain loyal subordinates.
Along with extensive background checks, trusted hiring agencies, and recommendations from other workers, this was what Oliver needed to go through to get hired as a gardener's hand in House Moore.
