Jeff,
I didn't read all 10 pages of this post & you could probably care less about what I'm going to say. But why would you take your son on a high fence hunt that he may shoot a 150 class deer at when he doesn't really spend much time hunting now. If he wanted to hunt it sounds like he could do plenty of it around your place. No he probably wont get a big buck. But let him pay some dues first and show some interest in the sport.