“In High School he will be playing against older kids anyway”

The holdback kid won’t! That’s the whole purpose of holding a kid back. Your holdback kid will NEVER play up in age.

Freshman yr on JV he’s the age of a sophomore
Sophomore yr on JV he’s the age of a Junior
Junior Yr on Varsity he’s the age of a Senior
Senior yr on Varsity he’s the age of a College Freshman

It’s done to gain an unfair advantage. In other words CHEATING.