You're going to get a lot of different answers, which is the beauty of HSBBWeb
I've had 3 sons go through this decision on their way to high school baseball with one playing in college (oldest son). It was very important for my oldest son to play against the best competition (his choice). So, from 11U all the way to 18U that is what he did, and it pushed him to get better at each step of travel baseball and high school. It was the same for him with academics. He is a very driven individual. My middle son liked baseball alot but didn't love it. He liked to play good competition but he didn';t live for baseball.....he liked baseball when it was on his terms. He challenged himself more in the classroom. My youngest didn't play travel baseball or American Legion until after he made the high school team as a freshmen.
Three very different paths. We provided the level of baseball that my sons wanted in their young lives. it was 100% up to them.