It's hard to find good people who want to run for this office, unfortunately. Around here, that explains why so often our school board is comprised of retired teachers, and not independent-thinking, right-thinking citizens.
School districts are often premier employers in smaller towns. No place, except maybe hospitals, employs more people who will vote en bloc for the people (often from within their ranks) who will better their situation, be it in 'contract negotiations' (pay and benefits), working conditions (the new school that isn't really needed), etc.
Candidates in districts (counties, even) with a few thousand voters often end up facing a voting bloc of employees and relatives of employees that require a large and dedicated turnout to defeat.
Because these are local elections, time and place are often set to be awkward, not in conjunction with other elections, and poorly advertised, which works in favor of the bloc. Unions and teachers' organizations will heavily fund races to ensure that insiders get the job.
"It's a small club, and you ain't in it." (George Carlin)
It is hard to overturn that, especially when the school system insiders rely on their thick folder of credentials and decry outsiders as not familiar with the educational process, and thus not good 'for the children'.
It's an uphill battle, and going in underfunded is not going to work.