I taught in high school for several decades and can tell you I saw this shift happen over the past 15 years (by the way I saw my students were just using search rather than folder hierarchies.)
I went from teaching in a Google environment to teaching in a Microsoft environment this year.
Though Google now feels familiar and relatively easy (though try moving documents from one folder to another online...), I'd almost forgotten that when it was first introduced, it was met with a lot of resistance, and teachers and students alike were confused for years.
Microsoft spaces (Teams, Edge) are far, far worse.
Since the schools I've worked at run their own servers locally, I think using Nextcloud as your main platform should be very doable. The apps you can install are mostly very slick and modern. (I use Talk for calls now, for example).
https://nextcloud.com/blog/keep-your-data-in-your-school-use...
I see the point about the clunkiness of LibreOffice. But as a teacher, I see great value in thinking carefully about what you introduce students to, because once a decision is in place, the effect multiplies with each new cohort of students.
> refurbished hardware (a random mix of old laptops in a large-scale deployment lol)
On the refurbished laptop market, I see large amounts of the same series of laptops, often Thinkpads, for example. I assume this is because companies will replace entire collections of hardware dated for their purposes. I don't think it is too far-fetched to connect this market to schools in individual districts.
> a laundry list of other "technology solutions" which would be, obviously, impossible for a school system to smoothly maintain or even deploy.
When I started writing (and the other stuff that comes with it - planning, editing, posting, follow-up, archiving) I stopped making music, because blogging takes up a lot of time.
