From my limited experience, the highest rates of disappointment seem to come from 1) choosing the best scholarship when the school isn't a great fit, and 2) choosing the school because it's the absolute highest level team that made you an offer, regardless of your chances of playing or even making the team. I've already seen a number of these situations not work out this fall for 2014s.
wattsboro, the only thing I would try to fine-tune about that advice from the older kids is to try to find a school that you love, which also loves you back (for baseball). IOW, he doesn't have to settle for "make the team if you can" if he can find a school that he loves where he knows he can make the team, which might mean playing at a lower level than some other options.