That is the heart of the issue. Maintenance should not be so difficult. It has generally been a non-issue for most Linux distros for over a decade. Windows maintenance is difficult on purpose. There is an entire economy based on windows maintenance. It's not just a headache, it's like shooting yourself in the foot.
> There are hacks who call themselves "IT" and there are true IT folks who have the training and knowledge to do things right the first time around.
Since we are talking about public schools, I accept the reality that there will, more often than not, be a "hack" employed. Even so, their job should be that easy. The reason that it is not is that Windows promotes a culture of "hacks" and misinformation. GNU/Linux has the opposite culture, and it's free.