My advice to you is that if you intend to do this as a DIY project (and it sounds as if you do), then you need to carefully evaluate your child's strengths and weaknesses as objectively as you can-- which you've done pretty well already.
Secondly, ask yourself if there are "problems" there that you can do anything about with changes/behavioral modification, and learn about how to make some of those changes.
I'd (at least for yourself) set clear goals. How much of this you share with your DS is dependent upon his personality and maturity. For some kids, it helps to know that changes in parenting are related to our desire to HELP them in some way.
Does he see any of this as a problem? Or is there any chance that he could be behaving in this way because it produces rewards for him personally? You should consider what he's getting out of the behavior that makes him continue doing it.
It's possible that he's being manipulative (though not necessarily 'deliberate/cold' about it). For some useful tips on managing and defusing that kind of behavior in children, The Manipulative Child is a really good tool-- it focuses on removing the REWARDS for the behavior by changing parental responses to it.
