The last one was sort of a nobrainer, if a person struggles so hard to open up and as soon as she starts finds in her car panties from another woman... the only thing I'm not sure about (because I only did it once) is, did Cathy really remove her panties? All I remember is her blowing the MC off, but I have an horrible memory and for obvious reasons (Bella) I didn't play it in any other run.
Jill's picnic scene is probably indeed a bit of an "abrupt" event horizon "You didn't want to hang out with me for your birthday, you are done with me", even helping her for her concert doesn't change a bit.
I'm not too sold on the J&M rejection based purely on the DIK scale, in part because to a degree I think that scale is one of the few weak points of the game, most of the actions are really DIKish, but some are DIKish only because they can't be CHICKish so to speak, but also because while Maya prefers a more neutral/CHICKish MC, Josy celarly prefer the DIKish one, but I guess it tells who actually calls the shots in the couple?
If anything the one thing that could make more sense (but would require a different story etc..) would be if even amongst LI's and other characters the DIK scale and MC's choices mattered, I still find a bit "sus" that every single main LI ends up becoming friend with eachother and "hanging out" with the MC.
I do like the finality in the choices thou, if the MC screws up or simply decides to go in one direction rather than another, it should be accounted for, unless the VN is a harem sort of VN.