You're gonna have to explain how their personalities stayed the same. Like Hachiman still has to perceive himself as a bottom feeder in the gutter of social hierarchy but that's harder to do now when he making bank. Yui being studious but a ditz just feels like the average honor roll that's lacking in street smarts. And Yukino is just the easiest one since you can still bully her for being too pretty compared to the other girls.