i dont know how being sent to "time out" which is essentially what jail is, is going to rehabilitate a person.
Chances are if he had that much stuff he wasnt just some poor 4 toothed fellow. It does sound like he violated the most important rule in dealing though, which is dont get caught doing your own stuff

I am not particularly a fan of the 3 strikes rule as a felony can be as little as stealing a car, or 200 dollars.
Now, i can see three violent crimes and your out because those people are the true menaces of society, not some person with a little bit of ease up powder or leafy greens.
The part about being 1000 feet from a school is rediculous too if he wasnt selling to them. I believe they have a rule like this in public parks too.
sigh, fuck the reagan era