technically you could kill peasants and ransom them to hit 275 roguery.If you killed arounf 60% of them with a blunt weapon (or captured with doctor's oath) you could hit 275 roguery in...It is absolutely ridiculous that Raiding villages isnt the best way to level up roguery.
about 400,000 peasants. Get started! The reward will feel better if you earn it. That's part of the narrative.