coming back to the question raised by ... 
Francis7: "Anyone have any experience or insight on this situation at the college level?" How is the college baseball experience and 4 yr outcome effected by “bad team” versus “good team” factor?
When it is time for my 2024 son to make his decision - how much weight should the college program's "winning" (or losing) history factor into the decision?
Assuming all other factors being equal, Should I encourage my son to go to a college that is +200 miles further away from home to play for a program that has a winning history and to avoid a much closer to home program that hasn't had a winning season in ten years? My son has never played on a baseball team with a losing record, I think it is best to avoid a college program that has a history of not winning much.
My son's last losing season in any sport was in 3rd grade rec basketball season, only two kids on the team could dribble with their eyes up - I was the coach that insisted that all ten kids get equal playing time - we didn't win a single game, and my son and wife asked me to never coach again.