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For those who have been through this process, what would be your best advice on how much is enough and what, if anything, do you wish you would have done differently?
How much is enough is largely dependent upon what he is trying to accomplish, where you live, what schools he wants to attend and what level of ball he wants to play in college.
Without having this information, it would be difficult to give you advice.
As to what we would have done different, I can give you my two cents (that is all that it is worth).
The summer between my son's junior and senior year, he went to the Stanford camp (a must) and participated in three regional showcases. Additionally, he played American Legion ball. Out of it he ended up at a quality D3 school which he loves and is playing ball.
What would I have done different now is: skip the Legion ball, it was a waste of time given his objective to play College baseball. I should have put him on a high profile team that participated in the WWBA in Georgia and a few other high profile events. Additionally, I would have sent him to the PG academic showcases. Two of the three local showcases were alright, but I would have spent the time in writing coaches in advance of attending any event.
I would have also been more proactive in having my son write and call colleges. With any interest, I would have found a way to get him to events that they attended once they had acknowledged his interest.
In the end, he ended up at a great school, however, he (and I) are convinced that he could have played at major program if we had "invested" more in certain activities. The downside to doing more was the financial commitment which we really could not afford, which leads me back to your orginal question.
What should you do? Start defining what kind of college experience does your son want? What part of the country is attractive to him first and the family second? What are the financial constraints for the family? What level of ball will he be accepted (recruited) by coaches? (This very important, don't waste your time going down a road that won't find your son a school).