My oldest son had a very similar path @anotherparent. Almost identical. Some of the travel kids on his 15-16U travel team were getting attention from ACC and D1 schools as a result of winning PG National WWBA in East Cobb. My son started thinking seriously about college baseball at that point. He was already playing HS Varsity in a very competitive region in Virginia as a freshmen. My two younger sons had the advantage of seeing what their older brother was going through playing college baseball, and decided it wasn't for them. They didn't have the baseball passion their older brother had.
@theleica I think most of us understand where you're coming from. It is one thing for you to think to yourself that maybe he's got a shot at this, however it is another thing for your son to realize that this (college baseball) is something he could possibly do and that he likes the grind of doing it....because it really is a grind. In the last 10 years, the travel baseball investment and infrastructure has become ridiculous. 14U is a good indicator in terms of does my son have the skills and a real genuine desire to be the best he can be AND consider college baseball. Most of us that have been around can spot elite skills right away, but it is hard to know what they are thinking. As a parent, I would encourage you to track your son's progress and his drive & attitude toward achieving his baseball goals. As the saying goes, "attitude is everything". You're in the best position to know if there is a fire burning in his belly or is he going through the motions because of his friends. If the fire burns in the belly then maybe it is worth some of the (judicious) investment in travel baseball. The college baseball landscape is rapidly changing but there is always opportunity for skilled and driven young men.
As always, JMO