Thank you very much for your insights. Finding a solution that works everywhere is indeed very different from finding a personnal solution that will break with the slightest change.
I have strangely encountered none of the problems you listed. I have installed on several different machines and never found a way to broke the installation. But I guess 100 students are way more clever to find strange ways to break things than I’ll ever be. I agree with git and msys2 mix being a little bit cumbersome. Strangely, git depend on msys2, but installing both is always a clunky. I’ve always found that everything works better if I do everything from msys2, which is anyway general simpler than downloading 100 standalone package installers. But I guess it’s again too much expectation from students.
I guess using the default windows toolchain (Visual Studio with Visual C++ compiler and debugger) would be even more time consuming, and would require you to tell them how to write OS independent code, which is something I have very little experience with. Or have you considered it?
I would add that I wait with much impatience full native OpenGL support on WSL2, which will hopefully making all those things trivial.