Trust, great question...and Fenway has, as usual, a very thoughtful answer.
My oldest did not find the right fit the first time around. Way too focused on his relationship with the coaching staffs that were recruiting him, and not enough on the three things that Fenway talks about. Nor was there enough focus on faith/spiritual needs, character and community the first time around. Nor the overall environment of the schools, e.g., weather, facilities, etc. And my wife and I allowed him to lead down that path. It was a mistake.
For our youngest, we were far more prepared to look at the schools recruiting him beyond just academics, baseball, and $, and definitely beyond the personalities of the coaches recruiting him. We provided better guard rails during the decision making process. And now in year two, while nothing is perfect, the fit is definitely spot on.
My oldest is having his second chance with college and baseball. After a 2+ year layoff from both, he transferred in Spring 2017. Academics, baseball, and $ were still very important. But we elevated the other factors in importance and he's found a much better fit.