I work at a mental health treatment center and the school we have has a basketball team ranging from 13-17 (although developmentally, it's a different story). I just finished my first season with them and I'll say from the time they started, to the time they finished, there was some good growth. We didn't win any games but I'm happy that they grew as people so that's a winning season to me.
One thing I never got worked out was playing time for the kids. I'm in a 50/50 situation. I have a certain amount of kids who want to play and to win and I have kids who want to play just to play--winning and losing doesn't matter. Personally, I coach to win and I expect the players to play to win. I want them to be taught the effort it takes to have success and understand life because their perception of life and how things should be are heavily distorted. But there are those few kids who do their work in school (which for some is a miracle) and behave (which for some is a miracle) just so they can play basketball but they aren't as skilled as other kids. They work fairly hard in practice.
There is a constant war inside of me that says, "Let everyone have a chance to play. Who cares about winning and losing?" Then there's the other part that says, "Basketball is a team sport and the point of it is to win. In life, there are people who are more skilled than you at something and they get looked at/to more." The lessons of life learned in something that isn't really that important in the grand scheme of things.
Personally, I gravitate towards the play to win but if I can, will try to play as many people as possible but it's no guarantee everyone will play. But what I think about is the kids that simply play because they simply like the game. I can't blame them. It makes sense.