I would teach him how to shoot pool and play poker. The time he would be spending in school will be the time he practices these two games. After a few years of reading the right books, analyzing hands, working on stroke mechanics drills, he will already be talented enough to make the same money a college graduate makes.
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If he got a real estate license he'd make more than a college graduate makes.
Can you get one without having a diploma?
Depends. Every state has its own requirements (you could try looking here). You'd probably want to move to state that has a hot real estate market (e.g. FL, TX, etc.). Speaking a foreign language would be beneficial and set you apart from the competition.