meads,
It sounds to me like you are doing a great job of supporting him. As difficult as it is for a 16 year old boy to figure this recruiting stuff out I think it is equally as difficult for parents to figure out how to best help & support without causing friction. Videoing everything can be tremendously helpful. I'm currently helping my wife with her tennis game. I've played tennis my whole life and my wife has picked tennis up late in life. Recently, I began videoing her with a phone/tripod so she can see everything she is doing/not doing for herself then we talk about what she is seeing. She is learning much quicker this way. I got the idea from my college tennis coach who was doing videography back in the early 80s. Video really helps. All of my sons enjoyed seeing their baseball academy videos over the years and I think it helped them with pitching and hitting in high school. My oldest son would look at his college game videos as well mostly for pitching mechanics. There must be something in the human psyche to see yourself on video and quickly understand the difference of what you thought you were doing versus what you were actually doing.
Best of luck with your son!