An overall good story with some horrible writing elements, if I had to sum it.
First of all, there's the Aspen thing. A few days have passed since the sermon of his parents, and instead of trying to re-acclimate himself with his former environment, dig somewhat deeper into the company he's supposed to partially inherit, trying to reunite with his only living family member, the main character fucks off half across the country, without the reason for it ever explained. Looking at it from a third person point of view, it serves nothing but to derail the main storyline. Introducing Mallory and a sex scene with someone could've been done even without him leaving for Colorado for three whole months, and the story cohesion wouldn't have been screwed over this much. Of course, you could try to reason by MC running away again, which only makes him a little bitch that grown literally zero during that five years he was away. Although, I don't fault him for leaving back in the day, I'm not even on the team that thinks it wasn't the right move, it was, but this time it's a whole different scenario, where using it as a storytelling tool is just a bad move.
Secondly, there's the whole Jaye thing. The first update set her up as an unlikeable person, stupid at best with the whole inviting the rapist fuck to the graduation party and then acting arrogantly after the fight scene. While everyone likes a good redemption story, bouncing back from that is not easy, and if the personality keeps up, it will become impossible overtime. I get the jealousy part because of the kiss, but it won't absolve her from pulling a move like making Christian into her plus one on the boat, especially that she already screwed up twice since the MC had "returned" to home. That's a surely good way to write off the supposed main girl in front of the majority if the audience, and if the Chasing part in the title has to do anything with chasing after her, then the whole experience of the game will be soured, if the point is to trying to get liked by someone like her. If it isn't him that she invited, then it becomes a pointless cliffhanger, or a bad explanatory scene of why both George and the MC reacted the way they did. That is pretty much writing yourself into a corner.
A smaller thing, shounen harem manga level dense protagonists aren't a good even in those stories, especially not in a more adult themed one. During that five years it did seems the MC became somewhat more mature, regressing to that for storytelling purposes won't be funny, just bad.
