Here are my 2 cents about the whole messed up sitch...
Josy & Maya are lesbians so it's a no no for the mc, nothing serious can't come out of this trouple... the only thing that you can do is to tear it apart and one of this trouple will be devastated for life.
Sage is too jealous, the way she treat her previous relationship (with the binoculars, obsession and other facts) should be huge alert for her future boyfriend, despite that she is a nympho so if you want to end in relationship that you are cuckold or swinger... probably it's your girl. And I think she play a game on her own and she play it very well...
Bella is married and she is your teacher, despite the fact that she is pretty attractive and MC wanna bang her, the chances that this will end fast and bad with broken mc's heart are huge.
Jill is virgin, also the company she keeps are too way out of mc's league. He is uncomfortable there... the friends tho are the least problem that MC will face... the huge one will be Jill's family and family history secrets.
So think carefully what you want for your MC, but probably the best choice is OTHERS.