#3: I've never done the IMG Wood Bat leage because when I found out about it, it was time to showcase myself for colleges and such. However, I went down to IMG about the same age as your son is now. I spent 3 weeks down there apposed to the 8 week wood bat league, and I can honestly say it made me so much better. Now it's only going to be what he takes out of it, but if he puts in 100% it will be worth all the while. I would do it now, or 9th/10th grade summers.
Also, I have several friends from down there that have done the wood bat league and they loved it