Jill - Exactly.
Bella - The problem is there is such a lack of "good" older male characters around. Maybe Neil still has some juice in the tank, but that's about it. I still think if MC doesn't save her from whatever mental health crisis she's having, then she's lost. That school library scene with future MC talking solidifies it for me.
Sage - Probably right, but definitely not someone at B&R. She's going to focus on her coursework for her last semester if she gets over Chad and doesn't stick with MC.
Maya/Josy - Honestly, I can't see any other outcome than the two of them staying together. Either a throuple with MC or a couple on their own. They may "break up" but no other dates at B&R are gong to compare, and in the end, they are getting back together. I have a hard time seeing MC going off with one and leaving the other. They are a package deal at this point and forcing them apart to steal away one of them would be a shite thing to do to the rejected girl.