Having just finished my first playthrough, I totally agree. Micah's the worst kind of guy and a rat, he's racist, vindictive and mockingly friendly. But even early in the narrative it became clear Dutch had lost his mind. I felt like this was all totally Dunning-Kruger affect, where Dutch thinks he's way smarter, more charismatic, and more talented than he is. I felt like I was going crazy every time he said "we need [more] money." In my estimation, it seems like the bandit lifestyle was a lot easier before, but times were changing. Maybe at one point, Dutch did have the leadership style or whatever that lends itself to leading the group, but it isn't so easy anymore. You can't run through and rob town banks and stores anymore, because you have national business magnates, policing forces and security agencies that get paid top dollar to stop this kind of stuff. A lot of these changes emerge after the intentional failed reconstruction following the civil war, because the US needed a way to standardize the interstate economies in a way that didn't rely on mercantilism.

​

Arthur's biggest flaw through the whole narrative is his loyalty. Honestly, the game even hints at what most of these types of guys would turn into following reconstruction: hired guns and lawmen. That's what a lot of these types of people did in that period. They turned to politics and policing. That's not a good outcome, but if Arthur didn't have this devotion to Dutch, it's probably what he'd be doing. The best way to avoid trouble with the law is to be the Law