For instance - OS X window managers suck. Do you think that a project like Spectacle should have never been built because they're just picking up Apple's slack?
Microsoft is very happy that Node, Java, Clojure, etc work on Windows. It helps them a lot. But they make little to no effort to help bridge the gap, they usually leave that to everyone else. That's my gripe, right there.
And to be fair, this is not a black and white situation. It's complex and Microsoft's role in all of this is complex too. And sometimes this issue does crop up on other OSes, for example Docker on OSX is sometimes a little painful.
OK, but that's also where you're wrong, right there. In general, but also particularly for this exact issue - Microsoft considered attempting to fix the file path limit for the first release of Windows 10. Maybe you don't understand, but it's going to take a herculean effort to fix this. They want to do it and if you need proof of that I can find posts of them talking about what I just said.
Why they can't fix .Net under the covers to use UNC in windows to avoid the class of problem I don't know, understand or comprehend... and that's just one very common platform for windows. I would say the same for npm/node and libuv for that matter.
I use bash a lot in windows (installed with msysgit), and that's got it's own set of problems. More problematic is the number of node modules that rely on bash scripts for builds, that don't work at all in windows.... which makes it very hard to contribute.