While I'm not the biggest fan of Josy, I think it would kind of break my heart to see her go that path. But I'd rather see Josy go that way instead of Maya myself if there was some choice to be made.
My suspicions is that Chloe is in deep with someone who she owes money toward (hence her scheme/phonecall) and ends up abusing Josy/Maya (Since the josy/maya thing is already a "loose" form of NTR, I can see them getting pimped out because they're desperate, which is a full stop for me).
I normally gravitate toward either the good girl with hidden scars (Maya or even Jill) or the bad girl who's hurt but just want love (A Chloe type without the "evil-ness"). From what I can gather, and I'm likely wrong with this, but chloe is just bad news for the two. And knowing my playthrough of AL, I'm leary of what's to come. I'm kind of pissed off how "accepting" the MC is toward the whole ordeal too.