I'm not as negative about it as I seem to make it sound, but it blocks the story from progressing and that's the problem I have with it. Make more cosmetics and add-ons to buy with it, great. But don't leave me grinding just to try and complete the story. That's bad design, in my opinion.
It gives you time to work on the other girls, and just have fun with them. You are not supposed to focus on just one person.
There are a handful of story events that cost money, and several of them are kind of expensive if you are not 'rich', but most are later on and they are not all required, like I did not have to spend a few thousand in a recent Ashley event, but I did anyway.
My only issue is that I would like events like that to tell you before you start them, so you can plan for it. Not start them until you are ready. Can't remember if he said he was going to do that or not...
One idea that could make money management more engaging (and realistic), could be that of letting the MC go into debt if he mess up, and Trenero could back it up only through advertisement. This way, more clients would flock to the bar, but that would mean the MC should employ one or more girls as staff, and their profitability would vary depending on how well they have been trained and are in love with the MC.
I thought that was an option, at least once... I remember something with Ellen about a debt forgiveness or something... Never had money issues, so I have no idea how it works though.