*Mild spoilers for objectives. It's basically impossible for you to stumble onto this challenge however. You have to

I haven't attempted it yet but what a cool idea for a challenge. And the name is perfect. I won't say I fell out of my chair but I was like "Damn, that's good."

There is a similar one in Whittleton too.
Basically doing good stuff for bad people.

@personandstuff: I plan in taking a pretty deep dive into H2 over the next week or so. I did a few of these on my first playthrough, but not all at once. It's a fucking great game.