That's just gamey stuff though; it's just easy to break the game and earn shitloads of money once you know the best jobs or places to do it, but earning that much is not tied to the narrative at all since it's still a misery simulator in concept.
Maybe a fix for that would be to have a proper hardcore mode more difficult all around: reduce the money that can be earned (or exploited), remove the cap on Bailey's payments and let it increase infinitelly, etc.
Then again, the game wo0uld really benefit from having long-term "goals" or endings if you will: objectives that we can work towards and "win" the game. One of those endings could very well be you overthrowing Bailey and saving the orphanage but my guess is that since the game is in theory very early in development (despite the huge amount of content)
Vrelnir didn't have time to implement those endings yet... tough I dunno if he ever plans to, or if DoL will always be just a sandbox with no proper endings.