Hi and welcome to the posting side. Considering he is targeting IVY or HA D3, he has time. Combining that with the concerns you state about "playing to please rather than himself", I would continue to be patient. While baseball can help get students into certain schools, you know well that it is a heavy commitment and the desire needs to exceed the notion of using it as a vehicle to get in.
No doubt you are plenty capable of evaluating the numbers, skill set and projectability. I suspect he is fine in that regard. I just get the impression that he still needs to come to his own conclusions about what level of commitment and love of the game he ultimately has. With continued positive experiences, that will likely grow. If he feels pushed, I suspect there is a chance that will retreat again. You may want to gradually feed him the information he will need without pushing... "If you decide you want to pursue... be aware..."
Cool that he has reconnected! Hopefully, that continues to go that direction. At some point, it usually clicks one way or the other.