Honestly, I think the bank job at the beginning of the game as part of the story being removed could fix a lot. Nothing makes sense when the plot revolves around making more money and you have so much you never have to worry about it. I thought I accidentally found an exploit or something.

But there's so many strange ideas. Like you reach st. Denis and are able to buy fancy clothes, but your character looks like shit at this point which ruins the whole thing. Who thought that was a good idea?