Missed the fine print when signing up for the trip to Rapechester, eh?
I get that this is a major point about the game, but it's also the major thing that pushes me away from DoL. And, frankly, I have a hard time even understanding the reasoning.
An opressive world where you are really struggling, that's all fair and well, by why not offer a silver lining at the end. It's human nature, that's why happy endings where the norm in Hollywood for the longest time.
Humans (men especially) are also problem solvers. And that's why players generally find ways to deal wirh what the game throws at them. Like others remarked, it's not that hard to progress to a point where Bailey is easily paid off. It's more difficult (but also possible) when you also have to shoulder Robins bill, which is why I just ignored his suffering in my last playthroughs.
When the player has found a way to deal with the oppressiveness, they no longer are oppressive but merely annoying. It's like a missing endgame. Getting rid of all that crap should be the end goal, you get some ending closure like in Fallout and ride into the sunset, done, time for another round.
As it stands, my playthroughs just kinda fizzle out with a giant "fuck that shit".
Maybe I'm weird.