I wouldn't go by how old the actor looked as any kind of indicator as to how old his character actually was supposed to be. Almost all the cast members who played the Rydel Senior High class were older than high school age, some quite a bit older. A few were in their 30s. So it's not unlikely that Leo/Craterface was supposed to be high school age as well, even if the actor wasn't.
I always surmised that he was the same age as kids from Rydell because the Scorpions and the T birds seemed to be rivals. I don't imagine someone in his 30s wanting to "rumble" with a bunch teenagers, so I always took it that the CraterFace and the Scorpions were a gang from a another highschool in a different part of town.
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