Congrats to both of you! These are great times. I'm not sure our experience compares as my son was recruited as a position player but had the same "mix" of offers you are considering. Many recruiters/universities view Pitchers differently.
We really didn't covet JUCO offers (2010). If you are looking for the best financial circumstances (24 scholarships in come cases), while remaining Draft eligible, then that seems a great route given your circumstances. If it's education first, while playing baseball, then that may affect your considerations? How your son projects, how much exposure he's had, and the amount of interest he's getting all factor into this.
Mine had D1 interest from what I will call Academic and or cold-weather programs. The academics certainly fit into our thinking but "cold weather" didn't fit into his! Also, a local "urban" D1 program was very interested but that held no appeal for him!
Very early a nationally recognized D2 program rose to the top because; they recruited early (July), aggressively (full tuition) and were highly touted by all the "expert sources" we could muster. They too had other options, besides my son. They didn't rush us but were honest in saying they would go with players that were interested in them. No deadlines were spoken but we knew we had weeks, not months to ponder. We did not feel there was further negotiating room. He verbally committed early (by August) and had no regrets when the phones rang later. That University offered his preferred curriculum, was near enough we can watch him play, and offered the type of Campus experience he was looking for. We consider it a Win-Win. Conversely, friends of his just had to "experience the large D1 atmosphere" and waited. A couple of those players are now very disappointed. You just don't know. There is risk in deciding too quickly and or too late.
One must consider all those things before "he makes up his mind."
Best of Luck!