There are many. Unfortunately both the domain-knowledge requirement and switching costs are very high. It's hard for a newcomer to break in, and once they have there's little incentive to keep updating the product. The result is a succession of companies and products that were probably fine for the time when they were introduced, but quickly seem dated as the rest of the industry evolves.

The other alternative is open source. Lower the initial cost of entry, amortize the cost of maintaining and enhancing core components, and let vendors compete on the basis of what they can offer on top of that. Unfortunately, this approach yields much lower margins than what "vertical" software vendors are used to, so they'll fight any such thing tooth and nail. That gets us into the domain of trusts, cartels, and regulatory capture. The business factors preclude technical solutions, and users pay the price. :(

School choice: spend money upgrading a system that seems to be "fine", spend time and money training personnel on how to use the new system, and cut classes of your choice angering parents.

Or, just keep doing what they've been doing.

Seems like a pretty obvious choice, even if it doesn't feel "right"

To a certain extent, yes. But having experience in dealing with schools for IT (in NZ), you'll be hard pressed to get them to spend money on upgrades when the current solution "works".