First welcome aboard. Absolutely have your son try out for JV and also play on a travel team. Depending on the high school’s program (good/sloppy) in Chesapeake, really doesn’t matter, they will be playing ball. That is the ticket, play, play,- play as much as he can or you can support (money
). My son played JV ball when he was a 8th graded and started every game. The HS team he was on was pretty bad. But, he was on one of the top travel programs in the country (Richmond Braves). We did put him in Greenbrier Christian when he went into the 9th grade though. There are some awesome programs in the Chesapeake area; hopefully you live by the right school.
Playing up or down didn’t hurt my son at all. It’s all about the other talent on the team.