Been where you are at CoachB25 except there was no pressure to win. Coached middle school boys basketball first year and lost 3 games, lost 4 games second year. Became head baseball and the most wins ever in the school in one season was 11. We went 23-3 and lost 4 games second year then we moved. The biggest obstacle was teaching them how to win. The school had lost for so long in everything that they forgot how to win and baseball had never won so no one cared. Now it is back to where it was. No expectations and no winning. I believe expectations have to be there in most cases for a team to win.
There are a lot of smaller jucos that are run like a big high school but no expectation to win and they don't win. I think you find it in most colleges that have a JV. As long as you bring in money, we don't care. But at some point once you win there is a huge expectation to win. I've seen it watching programs for years. I've always believed you don't want to be the one who follows the big time winner as a coach. You want to be the one who follows the one who fails following the big time winning coach. He gets beat up for not winning and you only have to win a little to be liked, to start with. Nobody will want to follow Saban at Alabama, except for the money.