I think it's a matter of taste, mostly. Out of her branch, she rely on Bianca, she's the one who picks out her costume. She feels uncomfortable in it and first thing she ask MC "Is it me?" In her branch she rely on herself. Yes, banana is weird, etc, but it reflects her personality. Honestly, I don't think that she changes and becomes better, while staying alone. At the end of the game, perhaps we will have an option to become someone's cupidon, like we had in AL for Liam. In such similar case I mean Rusty. While we out of Jill branch we will have and see only canon content with her, so I don't see how it will develop and how DPC would show us that better Jill.
Regarding the rest - walk of shame, etc. Different girls handle this situation differently. Sage and Bella doesn't need MC as their white knight, they are able to protect themselves and have more than enough voice for it. Jill is the opposite. And Josy & Maya is somewhere between.
I mean that it won't look cool if all girls will have very similar personalities and will act in the same way most of the time. Differences in appearance is quite not enough for decent plot and gaming experience.