> other high performing students might not like him because he's a curve-breaker

Not that common in high school to have classes and exams curved. Also kids don't care.

> teachers would know what the family was up to and could view it as distasteful

They also don't care

> if the student went to UCSD or another school where this is a well-known hack, there could be stigma for having gamed the system/being less-smart.

College kids also don't care and there are lots of other ways to game the system. Ocne you're at school, no one cares who gamed the system to get there and how they did it