1) There is no single path that is best for your son. You have to be flexible and revise your "plan" when Stanford doesn't call. The dream can be a moving target from day to day, and its a crap shoot for most. I still have a list of 30 schools my son was interested in, not a single one of those schools was interested
2) If D1 is the dream, its not over if there are no offers out of HS, there is a second chance: junior college, You are cheating your son out of an D1 opportunity if you believe he's too good for a JC to even consider it, whether its his talent or academics. What a student gets out of a D1/2/3/JC is equal to what he puts into it. My son played with plenty of D1 players that were lazy, drunk, smoked pot and took easy classes......and went nowhere.
3) The process never ends. I have observed unless a kid throws 95, the kids who advance are generally the kids who work hard at it everyday, not the kids who think they can just show up and be the best, those kids are far and few between.
btw my son chose to play for a last place D1 school rather then a team that went to the CWS all the time. He picked the best playing opportunity with a coach he really liked.