Well done sir.
After a cursory look through the linked article, Connor's answer about playing both sports was understandably vague. "Working it out" between the coaches is open ended, but at the same time baseball has a roster limit. I'm sure there is a degree of professional courtesy involved with a fellow UI coach's son, but while Coach Heller is a positive guy he is also very intense. While he may want to accommodate the McCaffery family, at the same time his job is to put together his own team that can win games.
In the end it probably will come down to how much time Connor would miss during the fall, just as much as the time he would miss from February through March. At best he would step into a baseball uniform 4 (maybe even 6) weeks after the rest of his teammates have been practicing AND playing games that count on the schedule. That is a significant amount of time to try to make up. I'm not saying he couldn't do it, but it would be difficult.