Considering that we are almost half way to the 2.2 release date (Dec 2014), it seems like Windows support may end up becoming a second-class citizen.
It won't end up being a second-class citizen, it already is. I wrote about this 6 years ago(!) http://www.rubyinside.com/is-windows-a-first-class-platform-... .. shortly after that I ran a panel at Euruko where I asked both the audience and Matz their opinions for Windows support and no-one really cared. It's only through the efforts of a relatively small and dedicated group of people that we have Ruby running on Windows whatsoever.
The failing test for test_float wasn't Windows-specific (it looks from the tracker  that other packagers were hitting it even though it passing on the CI system used by core, its just that Windows users are more likely to be dependent on the packager rather than building from source without running the test suite, so RubyInstaller treating it as a blocker meant more on windows than other packagers treating it that way would mean on other platforms.)
Also, there've been a number of apparent fixes (the issue was closed 5 months ago, and then again 4 months ago), before it was (hopefully, finally) resolved four days ago. Its not -- well, for the last half or so of the bugs life -- an issue of no one taking time to fix it
> Considering that we are almost half way to the 2.2 release date (Dec 2014), it seems like Windows support may end up becoming a second-class citizen.
Irritating as it is for RubyInstaller users, this doesn't really seem to be a result of less attention being paid to Windows.
I'm sort of amazed they've made it run at all, the systems are so different. I'd advise anyone trying to run any of these systems on Windows to use a linux VM.
Nope: Windows support in Python is good and well-maintained, afaik. It boils down to attention for neophytes, really, and applications in education... a field where Python has much more mindshare than Ruby or node (IMHO).
Couldn't really comment on academic computing. I suppose, though, they are not really relying on the larger ecosystem as much as (say) web applications, so would not be affected so badly by the libraries issue.
The Windows support in Python is extensive enough I was able to write a web-client using ctypes and the native Windows network API to better support users with funky proxies and so forth.
Having heavy presence at a conference is clearly evidence of trying to get mindshare from users of the thing the conference focuses on, but its less clear that it is evidence of actual concrete work to get the related software working on any platform that you control. Is there really any concrete signs of Microsoft working to get Ruby working better on Windows?
Nancy's own wiki gives instructions for hosting Nancy on Ubuntu that start with downloading and compiling the latest version of Mono. They continue, "Open VS2012 and start a new console app NancyDemo.sln". Indeed, if anyone can successfully develop a Nancy application on Ubuntu, I'd love to know how. I spent two days yak-shaving NuGet (I even submitted a pull request to fix one bug) before concluding that it just doesn't work on Ubuntu.