I know people are saying Jill's route changes the MC, but I was just thinking what if a Jill MC is actually closer to canon? If the MC never got into the fight that led him to meeting Zoey, he would probably be more goofy...I mean he probably would have gotten his humor from Neil so that silliness is always there. Zoey taught the MC how to be more DIKish than he was but he's always been "more emotional" so how he behaves on Jill's route isn't necessarily Jill changing him.
Jill's route also leans into the MC's musical abilities more than the other paths thus far. Sure, you can teach Sage how to play and play for her but every other MG route you only play for them like once or twice, so music takes a back burner. I think it was sometime in early S1, but I recall him saying something about music being his passion. If you totally ignore Jill, you probably wouldn't practice the song for her or help her overcome her stage fright. Then no one on campus, outside of the MGs, knows how good of a musician the MC is supposed to be. Also on Jill's route, he plays a song he wrote. All other paths you don't know he dabbles in songwriting.
I didn't get Jill ragging on Derek in my playthrough but I almost never choose scary stories because it just seems stupid to me. Unless you're really angling for some possible Vixen action by way of shots, there's no point in choosing scary stories to save money for the CUMpetition (not playing mini games at least).
You could also argue Sage's relationship is more canon since you can get her anywhere on the Affinity spectrum and you get the second amount of music content with her. The MC will chill with Sage and play guitar for her regardless of whether you're on her route or not in S2. Sage and Jill are the only ones that you play guitar for, outside of free roams and regardless of the MG you are pursuing, if I remember correctly. I think they are also the only ones that you tell about not liking your birthday.
