So we have a similar school. Large classification, but low participation. We are constantly out talented by the schools we play. We have some programs that win, year in and year out. And some that struggle to win a handful of games. What's the difference? Coaching. The winning programs have over dedicated coaches. They are 24/7, 365 days all about their program.
I look at our baseball program and I see so many missed opportunities. And to me, it all starts in the off season. Our off season program sucks. If I was king, the first thing I would do is get my pitchers and potential pitchers into a weekly clinic or lesson program. I would also find a way to keep the kids hitting as much a possible. Once official practice starts I am practicing as much as possible. I want my practices longer and tougher than the games. We are hitting every day. I am pounding the infielders ground balls. Those have to be outs. And when a kid isn't doing something properly, I correct it.
I wouldn't focus so much on winning. And I wouldn't call loosing a game a "failure." Winning is the result of a process. If you are doing the right things winning will come.