The scavanger hunt list for Maya was always intended to make her fail, Maya never liked the HOTs and Quinn neither liked Maya. Although if Maya would done the list on her own and with different persones, Quinn might have considered her as Restaurant material and free tution.
Rione always wanted Quinn to stop expanding and eventualy Quinn getting robbed, she had no more the money to give the free tution and raising her prices for drugs and sex would only bite in her ass.
But what surprised me is, even Quinn at first didn't wanted Josy, when Josy told her she was Tommy's sis, Josy became more a potential for Quinn to have some controle over DIK's and more over Tommy. But why put her then together with Maya, made no sense, because then she only just did what Tommy asked her, to make her fail. Sadly for Quinn plans didn't go as she wanted and both won the scavanger hunt and list.
And no I don't want to see Josy end up as a stripper or prostitute, but from both Maya and Josy, Josy is more free spirited and lower inhibition and would possibly do it, as she not so ashamed of herself and her body, while Maya still got restraints and wanna be the innocent girl.