3and2fastball,
So, looking back I think it is dependent on a couple factors. Travel baseball can be a money pit if you let it be. You have to tailor what you want to accomplish with what is available to you.
1) Some organization will lump two 15U/16U teams together, for practices, tournaments and showcases. My son's organization did this and it really helped the 15U team become a force when they turned 16U. They won the 16U PG WWBA Nationals in 2008. Initially, they took their licks at 15U in 16U tournaments then they were winning 16U tourneys as a 15U team. They got very, very good and very polished at 16U. My son wanted to play at the highest level possible and this team accomplished that goal. At 15U/16U, he had no idea what colleges he wanted to target. At late 16U/17U he had a much clearer picture, and realized we were going to have to do some things on our own.
2) So, I think it is important to understand (and hedge) what kind of school your son is most interested in , qualified for, and what the travel team is setup to do....who are their college contacts and where have their past recruits gone. Some college recruiters are local, regional and some are national in scope. So, you have to match the travel organization, schedule, etc....to the type of recruiter. This was something we learned along the way. My son's travel team was very successful in getting their recruits picked up by D1 regional teams, but they knew absolutlely nothing about high academic recruiting which is national in scope . We had to learn all of that high academic stuff on our own. In other words my son's travel coach was exceptional at what he knew, and opening doors for my son but it wasn't a fit for us. We had to made some "audibles" on our own.
3) If I could do it again, I'd probably do a couple small things different. But it was important for my son to play at the highest level he could at 15/16/17U. He wanted to challenge himself. For us, his path was forged from a combination of his 15U/16/17U travel teams efforts and our own efforts to find the best program in his intended college major at 16/17 years old. Truthfully, I believe his college recruiting coaches were impressed with the level of travel baseball he played and they knew he could be a successful college player at their mid-major D1 level with a focus on academics.
As always, there is no one approach to all of this. There is common sense, a gut feeling, and listening to nuggets from others that have been down the path before.
Good luck!