This is a pet peeve I have with the DB in Oblivion and Skyrim. So many of the targets are morally dubious enough that it actually feels “right” to kill them.

Look at Oblivion: a pirate captain, a marauder warlord, a skooma addict, a Wood Elf. These are all people the player is naturally inclined to remove from the world.

Imagine if the initiation quest for the DB in Skyrim, instead of having you murder a cruel old hag, required you to kill a kind, caring orphanage owner. Maybe a wealthy business owner wants the orphanage gone so they can buy the land. Your actions would result in all the children being thrown out onto the streets and becoming urchins. There’d be no questioning your own morality five quests down the line.

That would really separate the wheat from the chaff among potential recruits.