As for Jeremy cucking Ian, I actually think he IS the perfect guy because it hits all the stereotypes. If anything he is a cut above other "chad" characters here. A lot of games just feature a fit, hung guy whose sole purpose is to cuck the mc. In ORS Jeremy has a personality, a backstory, and frequently hangs out with his friends. We get to see how he is when hanging out with his friends, or when he trains together with Ian in the gym. He seems pretty fleshed out to me. What more can you ask for?
We must be thinking about different Jeremy's, because the Jeremy in ORS has shit-all personality. What does he talk about or have an opinion about that in any way tells us about or fleshes out his unique personality? Even when he attempts to have morals with the 'don't bang a mate's girl' thing, he's all too ready to disregard that if/when Ian gets with Alison, so this again just adds to his complete lack of personality. How is that different to the 'big black cock that could belong to any black guy' stereotype he's being compared to?
And yes, we hear that once upon a time he was a major nerd that, for whatever reason decided to get jacked and become a chad... but we don't know the reason
why, Jeremy never talks about that time, nor refers to it retrospectively, and most importantly, we don't see even the tiniest strains of that former 'major nerd' in the guy he is now. Yes, people can change pretty drastically over time, but doing a complete 180 without any indication whatsoever of who that person once was in only a handful of years is simply unrealistic. Realistically you would see some sort of indication or a 'slip up' betraying his former nerd-self. THAT would make him interesting, at least as a start - showing how much he's tried to run from his former image only to fall back into it at times.
Example: it could when he's just hanging out with Ian, Perry and Wade (or at least just Ian) where he can let down his guard, that we get to see glimpses of another side of him that he wouldn't dare show the ladies; and the indication that him being a chad is still something of an act for him and isn't him 'by nature'. Maybe being something he isn't naturally can even get a bit tiring at times (despite the obvious perks, which is why he does it), and he's still retaining some self doubt from the former nerdy him. Maybe he even misses some of the things he used to do as a nerd, or how he could just relax back then, and only ever confides in Ian about it because he's paranoid about his image. So he runs from himself, but deep down, sort of misses it.
That would actually make him a little more interesting - give him some actual dimension. Hell, If Ian became a major chad and his relationship with Jeremy was bad, he could even use his knowledge of Jeremy's background/who he is underneath against him in a few different ways.
Anyway, backstory is meant to give an insight into how a character became the way that they are, or why they are the way that they are, but Jeremy's backstory means absolutely nothing. You could get rid of it or have never read it and it wouldn't make even the tiniest difference to our understanding of Jeremy, because
there's nothing to understand. Literally every main character in the entire story has more personality then he does.
Funnily enough, if you did get rid of that backstory, you'd be getting rid of the only interesting and unique thing attached to his bland-ass stereotypical character. Something that isn't even being used. It's kinda sad.