I'm not certain, but I thought it's mandatory to date Jill even if the MC is a total DIK and Bella hates him. So I guess that's the best case scenario because Jill never really liked the MC to begin with. I'm still going to feel bad about it, though.
Yeah, that. With Maya it just seems to be a game mechanic that doesn't have any consequences in the story, but with Jill it obviously does because the dialog changes. If anyone really wants to make sure they could look in the code for some variable tracking if the player stole Maya's money, but I doubt it exists.