The Sycamore district is landlocked, no room for expansion. Moreover, it has a closed enrollment policy so the talent pool is limited to who lives in the district and comes walking through the front door. I will agree with you on coaches micro-managing. Are they afraid being fired if they lose? I'm a CPS alum who grew up in an era before open enrollment, coach shopping and all that crap. With the exceptions of Walnut Hills and Central Vocational, a student living in any particular geographical neighborhood had to attend that neighborhood's high school. (What a novel concept). More importantly the same varsity basketball coaches, win or lose, seemed to be at the same schools year after year. This may have been a product of the CPS school system being aware what kind of cards the coaches were dealt. Coaches may have left, voluntarily or involuntarily, for other reasons, but not for lack of winning records. I do not recall these coaches micro-managing to the nth degree for fear of losing their jobs. With this relative stability I also do not recall coaches job hopping at the drop of a hat because they think some other school system has a better immediate pipeline of talent.
I did get to see Monteverde Academy play in the City of Palms Classic in Fort Meyers, FL, a few years ago. Kevin Boyle, the Monteverde coach, stood on the sideline the entire game chanting like an auctioneer, micro-managing every pass. I don't think he was in fear of losing his job and probably could probably pick any five players on his team, roll the ball out there, and win the game.
Lastly, there are college basketball players and then there are college basketball players. What high school players from this area have gone on to be impact players at the Divsion1 Power Five level in even the last decade?