I get the feeling that in order to succeed with Jill in the long term (future seasons), you can't have anything in the MC's past or present that will turn her away (I'm taking a lesson from
Acting Lessons here). You might think she wouldn't find out about some of the stuff the MC has done, but I wouldn't put it past Tybalt to hire a PI to yank your skeletons out of the closet. With this in mind, I created a save for a Jill Only route and tried to avoid anything I think she hates, such as bullies and infidelity.
I figure she would understand some questionable behavior (after all, she laughed at the "naked on campus" story, although I doubt she would have been amused if the MC had told her about the lewd Camila/Quinn scene), and some acts were unavoidable (e.g., Omega raid). As for the rest, here's what I did/didn't do:
Anything I missed?