To the OP, it sounds like you have a number of good choices. Maybe the top 20 team would gain a lot more exposure than the top 50. Your situation too is different from my son's as your 2021 is on more of a showcase team (travel to tourneys, no league).
For my son, however, playing up was quite beneficial to him. He played on a 17U team as a rising 8th grader, and 19U a few years later. He was undersized, so the experience really helped him. I remember watching his throws from SS to 1st when he just started and telling him that his arm will get stronger and the field won't grow. I knew if he faced the faster pitching early, the exposure would help and he could hit any age. After all, that's college. If you want to play as a freshman, you'll be facing pitchers 2-3 years older than you. While his team played in a league, he supplemented by going to showcases where many coaches attended. These showcases too had a couple of recruiting classes. It also gave him experience as to what to expect in "skills set" portions of the when it matters. Again different set of circumstances.
For you, an awesome choice. You didn't mention, would his playing time differ on the two teams? Would he be playing the same (primary) position on each?