Bottom line is I am trying to advise and push to be proactive but I am not going to do the things for him. It's not my decision or my life and only he can make those decisions. I will be there to help but in the end it's on him to put in the work. So far he hasn't done as much as I would like him to but he is doing some things. We will see how it proceeds.
One thing I did early on was make a Google Spreadsheet that I shared with him. My columns are (from left to right):
School
Head Coach (had him put in name and email addy)
Special Teams Coach or Recruiting Coordinator (maybe pitching coach in your case) (in this tab put in name and email addy/twitter handle)
Have You Contacted (Y/N)
Sports Management Degree (Yes or No would be his entry)
Tuition (all of the numbers are posted on the school's websites)
Books & Fees
Room & Board
Scholarships (Estimated - pulled from the schools websites. Their net cost calculators usually give you a ballpark number)
Estimated Net Cost (Tuition + Books/Fees+Room&Board-Scholarships)
City
Distance From Home
# of Students
Classification (D2,D3, etc)
So I set this up and we both filled it in for schools he was interested in. It's been a good way for both of us to be on top of this.
One thing I discovered early is my son is not the type to actively just figure this out on his own. We had to show him the way, so to speak. So this spreadsheet was a good way for me personally to get a grasp on the nuts and bolts of the whole process and everything in black and white. It's really helped.