You're wrong, it's actually those small irrelevant events that can trigger an "existencial crisis", which is actually good. I don't like the fact that every character has some shitty background, especially the main girls holy fuck non of them seem to have normal families or even families at all in some cases. From a narrative point of view makes sence in order to keep things interesting, many people praise the character development of Jill this season, but look how many potential setbacks has DPC placed on her route, bunch of friends that covet her bf, Rusty being jeaolous her disfunctional family, the whole situation around her sister and the Jonatan guy now, without those all you have left is a normal relationship. If done correctly it won't hurt if dev does it for other characters if done badly you'll have something like Lily, turns out she was suffered bullying, that's why se acts like she acts.
Sure, some events
can. And you can connect anything to
anything.
But without proper setup, a consistent theme or conflict, of "this character is about XY and Z", you're fishing for random scenes of conflict, and then have to read into them to make leaps in logic. Think red string on giant picture boards...there is no throughline with Josy's issues to cause her to have an emotional or identity breakdown. You'd have to have some serious, consistent events, pretty much every time we see her, to make these micro conflicts into a big one. In reality, she's one of the happiest most mature main characters, almost stereotypically into the MC, very similar to Zoey. In fact, she may be a Zoey 2.0 later on if her crush continues and she goes through her own Interlude (oh god no).
And what you listed with Jill? Simple forms of conflict.
-Bunch of friends that covet her bf -- as with every path
-Rusty -- not even an issue till he brings it up during Episode 9's Hallowe'en party, and even then, has no impact on Jill's conflict or character
-Sister and Jonathan -- her sister is a thing with her entire family, and whatever her "moon" focus is in relation to seeing the MC as her "destiny", and that's core to her family problems and drugs. But Jonathan was just introduced via 2 flashbacks in Episode 11, and just an event she was hoping for (and it's a good thing of plot development, not a form of conflict).
None of these are related, or have a consistent theme to show a flaw that Jill possesses that is constantly attacked, where she'll have an emotional breakdown over.
You're also missing the Tybalt nonsense, which got in the way of her relationship with the MC, and brought them closer together, along with Tybalt's presentation which caused her to cry, since she is now realizing other women are after him. Tybalt is essentially a sacrificial lamb of comedic proportions, and thankfully fuels Jill's relationship with the MC, and Sage's.
DPC does have an outline, but he's filling in the blanks as he goes...