I can imagine it being like, you get enough rebellion so that people start demanding for bailey to give people an option, she denies it but people start getting more angry, we then get asked 60k to build Training grounds on an abandoned loft (that we can buy for 20k) and then we have to train all the orphans to get stronger and actually rebel against her (maybe even kill her but leave the option to let her live if people actually like her ((Which I don't see how)) ), and then if you let her live she says every single one of the orphans will pay and give the MC a long and raged stare, for then to proceed for another story quest where she sends thugs to kidnap MC, (triggering the "you are being hunted" in the city), and giving you a safe house of "Bailey's chamber" and making you her personal slave or some shit for making her lose the orphanage