I think it's fair to say that nothing will be as convenient as a single centralized body controlling all the data management, client software/hardware and services under one roof. Nothing, not ever. So its not really an incompetent market so much as an incompetent or lethargic school system willing to make deep present and future concessions for a one click solution. The complete package is the problem, not the solution. You can't provide a modular and open ecosystem of small, single-concern pieces of software and hardware that rivals the single-provider model. When a single-provider model becomes entrenched, it's near impossible for those modular offerings to take root as they won't interop with the defacto Google, by design. Our education system now has a MAINFRAME.
For all the mud Microsoft gets, their ecosystem was pretty modular because that was their business model. They're locking it down and becoming more cloudy every day, but for a long while, Microsoft didn't care what you ran, didn't explicitly track your usage and worked with a wide variety of disparate multi-vendor software. I'm not saying Windows is where we should have been nor that it wasn't a lock-in of a sort, but we're not really better off now. Apple iPads were less open than Windows, but had consistent hardware. Now Google has achieved the complete solution.
I think a large part of it is the framework v. libraries argument all over again in a different package. I think we're on the swing back now where we want to trust providers a lot more than after the corporate IBM fallout. With everyone getting their music from Spotify, movies from Netflix, games from Steam, analytics from GA, chat from Slack, books from Kindle, etc. Schools are asking, why not us too? For a lot of people, schools aren't something you can just decide not to sign the EULA and walk away from though.
These chromebooks are just cheap thin clients for Google services. They're some of the most locked down devices on the market, but thanks to the internet being decentralized by nature and Google seeming like the door to the internet, their centralization doesn't seem so scary. They interop with little else and hold no data, even printing hits their servers first before your school's printer.
Here's to hoping for a swing-back.