Who is actually having second thoughts, dad or son?
I think you need to talk, and you need to tell him it's not what you want but what he wants. I mean an honest talk.
There were solutions a while back offered about pursuing JUCO options(baseball) for your son. This can be a great alternative and your son can finish up his HS career the way he wants to (maybe forget the showcases that might not lead to anything this year). If your son goes to a baseball HS powerhouse school (in Miami) if he did well any JUCO in FL would sign him. I did tell you this and will again, my son has friends who went to JUCO out of HS, then onto that big D1 baseball program and now on ML rosters, probably not graduated but close to, but they took a route some look down upon and made it work.
Seems like you are putting a lot of pressure on yourself about this, and that usually trickles down.
Let him do what he wants, sit down and talk about how he can work towards a goal and still try to enjoy his last high school year.