95% The Pit (I realy dont get the so called moral ambiguity in that one. seriously up untill that point you have probably beenslaughtering Female Raiders by the dozens up to that point, suddenly the fact that you find out that one of them has a baby is an issue? Aparently they thought that all of the Female raiders up to that point were barre and or that the Raiders both male and female did not have kids of there own someplace that they might have cared about. Honestly how do you think a settlement like lil lamplight came from? no advlts, and as soon as your old enough to have kids out you go!
It's not about that really IMO.
It's about that Ashur wants to establish a town that helps people, he uses the slave thing as a temporary measure because no matter how much of a silver tounge you have it's going to be very difficult to convince a bunch of people to go to a highly irradiated area with a lot of hostile beings to repair a steel mill and make it functional.
It was easier with the raiders because he could promise them all the ammo they could carry.
Raiders probably saw it as a good way to get better gear and to always be sure to have ammo whenever they head back home.
And to establish themselves as a great military faction ready to crush and take anything in their way.
But Ashur slowly wants to turn the raiders over to the "good" side and have them as his own personal army to protect a city that BOS decided to burn down while it in fact was a goldmine.
And he wants to find a cure for the slaves and hope that he even they can be called citizens at one point instead of being slaves.
He even lets his wife do experiments on their own child for the sake of the people.
Wherner on the other hand doesn't give a flying [censored] about the town or it's vast amount of resources.
He just wants to free the slaves because it's "the right thing to do".
Ashur sees a big picture.
Wherner only sees now.
At least this is my interpretation of it.
(But it's been maybe a half year since I played through the Pitt so I might be a little rusty on the subject)