So the gist is strong system type thinking combined with perfectionist tendencies? Barring some other underlying issue, I'd think personal space to practice. Opportunities to observe others (children and adults) writing at various levels of skill would supply ammo for him to make a full evaluation/decision on it. Maybe paper and pencils in his own space with his own paper shredder so that evidence of his practice can be destroyed?

Just brainstorming, I've only read bits about the concept.