Outlets to bring him an interest are good things, but they don't address the behavioral issues. People tend to look for one solution to cure a myriad of problems, remember that he hasn't got just one issue to deal with, he has many. There will be many small solutions, furthering an intererst with guidance is a good step, as it opens eyes to a larger world. As that world opens up, other venues must be explored, and this has to be done without lecturing. I can tell my kids do the math homework, cause they need those good grades for college etc. The only thing they see of me is someone who works hard and plays hard. I don't want them to make the mistakes I made and finally end up gearing up to go to school 20 years later than they should have. So trust me one this, anything that even resembles lecturing will shut him down. He will close up, his eyes will glaze over and he will go to that land inside that we have all run to at some point.
I disagree with the course you guys are setting, this needs to be handled by professionals. If you do go through with it, I applaud you for being willing to help, but tread carefully. Please, think before you act, and then think again. I screwed my life up long ago, and am finally fixing all of it. My big fear now is screwing someone else up. Be very careful with this endeavor, because it isn't your future hanging in the balance.
You know of course that our admins will have to do what they hate, and delete this thread, as him seeing it would be very detrimental to what you are trying to accomplish.