I agree , have been saying for a while that having no consequence for Monica not raising Victoria's $5000, other than being able to apologise, hurts the game. Still think there should be a game over or a "sent to the farm to be continued in further updates end" like there is in the Marcus route if Monica fails to raise $5000 two weeks in a row.
On the conversation about some paths being dependent on others I agree to a point. However, I feel the Shiny Hole depending on Monica having connections with prostitution is logical. When you think about what Mr Berkelbauch wants or expects Monica, as the new manager to implement, her success in turning the Shiny Hole around to his satisfaction will need those connections to work.
I can see a future update, probably after the final choice on who to bring to dance on stage, that has Monica failing to please the banker and the path will end with Monica being fired and told never to return. Bit like sometimes Monica needs enough corruption to engage in some acts, here she needs some connections she has made through the game to turn the place into what Mr Berkelbauch and I assume we players want it to become.