They're changing it up a little this year, I hear. Gonna finally be able to enter and pay online. Also, I'm hearing that you will be able to apply for more than one location in each hunt category.
Your boy will be able to enter the youth hunt drawings, and you can also include him in the general drawings with you as well, if you want to. My son is about to turn 17, so he'll no longer be eligible for the youth hunts. We've had a lot of fun on those through the years. I'm sure you and your son will too.
My advice (since you didn't ask, LOL) is to not take hunting too seriously when hunting with your son. Let him explore. Let him be a kid and have fun. Don't put too much pressure on him to be still and quiet all day long. Let him shoot whatever is legal game if he wants to shoot it. Don't worry too much about trophy animals. Make sure you cut up and laugh a bunch too, even if it means you spook a deer every now and then.
Man, I really miss those days. We had a TON of fun. We still do, but it's just different when they're younger and everything is new. Have fun with it, and take lots of pics. They will be priceless to you later. These sure are to me. Forgive me for clogging up your thread, but I'm fired up because this is what you and your son have to look forward to....