Yeah, especially as it needs to get dark to be able to sneak into the barn to milk yourself, which takes an hour per session. And then get back home to rest, which may take 3+ hours. Thus, it's best to work on Farm on weekends or on holidays, so you're not too tired in School next morning. It sucks a bit that except for Eden's hut, Wolf Den and other places of false imprisonment, the Orphanage is the only abode for the PC to take daily rest. I guess it would nullify the game's raison d'etre if you could just move out of there and take up residence (even if only temporary) somewhere else, not just Alex Farm, but perhaps Avery's Mansion, the Brothel, one of the teacher's places, or simply sleep rough in the Park or sewers, etc.
As at the moment the only repercussions for successfully refusing to pay Bailey are their random attempts to pimp you out at night (which can be easily avoided with save scumming), perhaps their patience could finally be exhausted and they'd kick you out of the Orphanage with tough decisions to be made: whether to become a live-in whore, Avery's concubine, Alex's farming partner / livestock or a street urchin, for example. Of course, your relationships with relevant NPCs would play a decisive role there.
