Jenny is presented as a good person and kind person, is she flirtarious yes but she's not a psycopath so blackmailing and forced strip (because it's not censenting hen you have the menace of being expelled), that's seem out of character
My theory?
She is presented as a good person, but she isn't.
She has ulterior motives for accepting you into the school.
I think she orchestrated the whole thing between MC and her brother, so that MC is forced into seeing her as a savior, and the person allowing him to have a chance.
Further proof is dad's note, which she claims she would have given to you in the office, but couldn't because of her brother. She didn't have it on her. She saved that for her house, after humiliating you, when she reverted to "kind and understanding" mode, and used it as emotional manipulation.
Classic sociopath behavior.
Let's also not forget that, in the office, she could have explained (even while her brother was there), why she accepted him, and framed the idea that she was going out on a limb, and he DID attack her brother, so he was beholden to try to make her happy.... without that coming across as blackmail on her part.
Lastly, let's not forget the girls she has are all strangers to each other, and allowed in, like MC, despite being rejected, because she chose them. Either they also have to make her happy to stay in her good graces, or they are part of her plan, which we have no real reason to assume is a plan that is in the best interest of the school, it's students, or the MC.
Her brother is a piece of work, but an interesting twist I see coming (and am maybe spoiling) is that he has good reasons to loathe his sister.... good reasons to try to stay at least at the edges of her good graces instead of being actively against her, and that he is being genuine about having a vision for the school.
I don't trust Jenny. Everything she has done has been emotional manipulation, blackmail, and abuse of power. Her flirty nature and the congenial talk on her bed after working are just ways to break through MC's defenses and make him think she means well, so he willingly gives into blackmail and doesn't suspect her of manipulation.
If I'm right, I hope the game gives us avenues to learn the truth about her, and to work against her (maybe even with her brother), instead of railroading us into being part of her scheme.
And if I'm wrong, there is a lot of explaining and justification for her actions that will need to be put forward at a later date, if things aren't to be re-written.
Personally, even if all it lead to was a second "bad" ending, I would have loved it if, when they demand you strip, the MC had the option to look at her and say "If your brother had allowed a girl who was rejected to join the college, and then took her to a house of guys, and demanded she strip and work for them as a nude maid, else she'd be kicked out of school, anyone who knew about it would rightly think he was a sexual abuser, and potentially a rapist. You think I should just enjoy this because I'm a man, so I should be flattered women would want to objectify me like this. Your brother was right. You are a slut," before putting his shirt back on, and leaving.
I mean, seriously. The threat that they could keep him out of all colleges... so what? He has hands on experience running a farm, and we haven't even been told what he'd want to do in college. Dude is just going to get boned with debt and a liberal arts degree. He should tell Adam and Jenny both to fuck off and die, and move on to a trade school.