I've given up and taken the hint about being a white hat, gone mischievous darkside
. It's actually loads more fun, like encountering a guy with his leg in a bear trap and choosing "antagonise" so that you're just like "Lol look at u" then putting the poor fellr out of his misery and stealing everything from his horse.
I mean if I'd tried to help him I'd just have accidentally killed him anyway... Why prolong it?
I also just did the first mission in Strawberry where you get a huge bounty and, as I was wanted there anyway, immediately snuck back into town under the cover of darkness and robbed the stores
.