some additional thoughts for prolonging the story and scoring brownie points with the sisters and especially mom:
I don't think mom should lose her job at any point (would be too much like BB) but perhaps some one time events come
up that require great sums of money that you need to either gamble for (casino but chance to lose all your money too), work for (pizzeria), or even sell your body (maybe some hot milf that's neglected by husband needs some young cock)
fortuitous events such as Ac unit broke and they need $3500 to pay for it, or toilet got clogged again because three girls showing = lots of hair in the drain. or Veronica's car breaks down and she needs something replaced but it costs $1000. getting these life events paid for (without cheating or maybe you can only cheat a little for the achievement to unlock) would give you major points with whoever is affected (maybe for Ashley she needs money for books or whatever)
I think making the MC work to make sure you can meet these one time events makes more use of hustling for money more worthwhile and there are very special awards for doing so. (in terms of special selfies or photos of naughty bits or sexual favors)
or whatever just thinking out loud again.