In terms of outcomes or results, I think coaching is underrated in importance in HS, travel baseball and College. I think it is overrated in importance in the Pros in terms of overall results. In my experience, twotex's championship results are more the execption than the rule. It is very difficult to overcome bad coaching at the 14U level. BTW....Twotex congrats!
My two cents...I would look for different things from different coaches at each level. For travel coaches up to and including 16U I would look for skills development, and do they make the game/team enjoyable. 16-18U showcase teams is about connections to college programs, coaching your son on how to find a good college program and some skills development specific to their position. A high school coach doesn't necessarily have to be good but someone that encourages him to get better on his own (weight room, training, nutition, possible private lessons) and opens the players eyes to what may be possoible at the next level. College has position coaches and head coaches. Your son will be spending alot of time with the position coach so it needs to be somebody he is comfortable with, and someone he can continue to learn from. The college head coach has be able to manage a game, manage his position coaches, recruit and keep the money coming in from alumni and the administration.....and did I mention win!
Can't comment on beyond college coaching. But it appears that at the MLB level the position coaches are real important and the head coach is more about managing the position coaches, egos in the dugout and the media.
I would not want to walk a mile in either my middle son's (high school) or oldest son's (college) coaches shoes. They have a tough job. As I've gotten older (I don't know about wiser), I'm giving my son's coaches a little more slack in trying to understand how and why they do the things they do.