someone needs to take the time to go to the meetings where the decision is made to go with one solution or another (and out-sell the person who is selling the alternative)

personally i feel i'm the only person in the district who is aware that there are email providers aside from gmail/yahoo

i haven't been following this story closely, but i always use https://www.google.com/search?q=foo&udm=web and it works fine.

School districts having the ability to pivot is not really a thing. There are many layers of entrenched interests and management to make a state or region-wide change. Some of this might be nonsense administrative overhead, but at least part of it is motivated by being cautious with education.