Tribal - my heart goes out to you. Just wanted to say that. I have a 25 year old son & a 13 year old son. Been through this before. 25 year old is doing great now, he didn't play any sports in college (other than some club rugby and a lot of weightlifting, the dude is built like a tank) and wanted to focus on academics and fun. He is thriving now, in grad school and doing great. Most importantly he is healthy & happy.
I have no idea how far my 13 year old will go in Baseball. For all I know he's going to be done with Baseball at 15. It is his choice. From what I've seen it is pretty clear he'll be good enough to play in high school even if he doesn't work at it much from here on out. Again I'll repeat: it is his choice, his life.
My main objective is to teach him to work extremely hard at the things he is passionate about. Right now that is Baseball. For all I know at 16 it'll be acting, or playing guitar, or playing Volleyball, or maybe it'll still be Baseball. The main thing to me is that the kid is learning the value of hard work