My last windows development experience is a bit dated and many things happended - especially WSL happendend. So what I have to tell is cum grano salis. My last experience is from late 2014/early 2015.
I was a Java developer - no problem here. But what made me go away was, that I was a) accustomed to a linux shell (cygwin is no help) and b) part of my toolchain - e.g. git - needed a minimal unixy environment done with MSYS. And the really awkward part started, when you whad severeal MSYS environments on your machine which interfered with one another (+ your cygwin environment) and required you to carefully rewrite the sequence in the $PATH (what should trump what) so to say.
So doing Java everything was fine. But doing additionally scripting in ruby and having somewhere a perl in your cygwin could make your life harder.
My conclusion is:
developing C# in windows with Visual Studio (Professional) works like a breeze and has everything to offer, to develop for windows
developing Java is nice under windows and linux as well. I experienced no differences
using something like ruby (or e.g. python had some known bugs on windows and who cares for that?) in combination with other *nix-centric ecosystems made my life harder as it should be
From my experience, *nix systems were per se developer centric - you could fix your own system, if you leave apple out in this point - and offer a rich integration, which microsoft for years neglected.
Only the last years, they are going to reconquer developer's hearts with WSL.
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