I've walked a mile (probably more) in your parental shoes. Play high school baseball would be my advice. It gives your son different and new experiences than he can get with his travel team.
Here's the funny thing...my son got to choose his high school. He could have played for the best team in the district (1.5 miles from my house) with the best high school coach in the state in my opinion. He didn't. Yes, it was painful at times. Once the travel and showcase season rolled around, he was always very excited to play a higher level of baseball and get the exposure we thought was necessary.