When my son was a HS sophomore I went to watch a game between the school he eventually ended up at and the team that was the runaway #1 team in the league at the time. I went in with my eyes wide open and really felt like I had a handle on what he could do and what he would be able to do in 3 years when he was a college freshman. I went to the game just to watch and compare what he was to what they were. The game was a disaster...18-14 or something like that....12 pitchers, 28 hits, 7 or 8 errors, mostly by the IF on routine ground balls. I went home and told him "yep, you can play with those guys". Obviously every game in their league isn't like that, but it's not like he was trying to play in the SEC lol. Some of the games he's had the past 2 years have been exactly like that...some have been very, very good. I would suggest that any parent go to a game or two at the level that your son wants (or thinks he can) play at and take an objective look. If you go to a D1 and just sit there thinking "man, my son can never hit this guy" then maybe your son is looking in the wrong place. If you go to a bad D3 game and think "geez, this is worse than HS" then you know that too....and maybe somewhere in the middle is the best idea.