In my little league years and middle school years, I liked playing for the coach who knew what he was doing and understood the game of baseball. (well, who doesn't?). But this guy was hard on us and had high expectations. He mixed a dry humor with a playful approach to treatment of his players. He didn't get red in the face and start yelling obscene things when something went wrong. He congratulated a good play.
One great play I remember vividly was when I was on 2nd base (60 ft base paths remember) and the pitcher and 3rd basemen weren't looking, I stole 3rd when the guy wasn't even looking. He looked up and was like "where did you come from?".
Also, I was really tall and played 1st base. His son threw one way over my head and made the stretch. He ignored his son making the play and made a wry remark on my tallness and the catch.
He always encouraged. I didn't hit a homerun that season I played for him. Every game, he would tell me "_____, you're way overdue."
He understood the game of baseball. He managed the team and played the power hitters deep and pull hitters the pole.
My favorite thing about him was the fun and competitive games he gave us. The best was one where he would hit popups to the infield and we would throw it to home plate, where there would be a bucket we had to knock over. I loved the challenge.
Also, best thing was the cup checks. I always wore my cup.
Worst coach ever was the one with a spoiled son. He had the best bat at the time, the stealth composite (red and blue). He played him every inning where he wanted, even if the kid sucked there. And when I told the kid how to play the outfield, the coach still let him play the ball incorrectly, allowing a flyball to become a single.
As I got older, winning became a bigger factor to the experience. It really depends on how each child is brought up. My cousin cant stand not winning. I have to play easy every time. I learned early on what it feels like to lose...my older cousins weren't so easy on me. The most enlightening part of playing little league is the people and the development of the friendships and the sense of comraderie.
One big thing that came from the game was respect. When I tried out for my middle school team, all the jocks were like "this kid is a nerd. he sucks." I'm asian. But, i ended up with the highest average and this gave me new respect among my teammates and my grade.