Not trying to start a huge controversy here, but just curious about the mindset of the community.
I am a long-time Windows user, I use mostly it (at home and at work for my desktop), although I have experience in Linux and have a personal server running Debian.
For several reasons, for the last ten years my experience with Plone has been about 70% of the time with Windows, and 30% Linux. In my personal opinion. using Plone in Linux is way more comfortable than using it in Windows. There are lots of documentation and support around the Internet for Linux.
And it "feels" like Plone, as a product, "prefers" Linux users. On the website, one can find installers for Linux, but not for Windows (I mean native installers, not the vagrant install kit). Also, there is the "promise" of a future installer, that never came to be ("We anticipate having a binary Windows installer for later releases")
For people running older versions, upgrade can be really difficult and/or counter-intuitive. For the 4.3 branches (which some add-ons might require), the Windows Plone needs IIRC python 2.6, which is not available anymore.
I wondered that maybe the community should simply drop the Windows support. It would enable the development of Plone (specially regarding the installers) to be more focused.
I think most Plone developers are on a Mac, then second largest group is Linux. But there are some in enterprise environment developing on Windows and - as far as I know from my customers - this works.
Just there is no installer. So buildout need to be used directly. This needs more knowledge about the internals than one might want to know. But it is usually not a stopper.
I do not think we should drop a platform. This will reduce not only the possible target group, it would also reduce the quality: writing code platform independent needs a broader sight.
I do my local development on a Windows machine with a minimal buildout. Just running in the foreground, no service installed. If you aren't trying to actually host on a Windows server you are probably better off just using something like this http://docs.plone.org/manage/installing/requirements.html#minimal-build and running the process in the foreground.
Plone actually works much better now on Windows than in the past, mainly due to Microsoft releasing their "Visual C++ Compiler for Python 2.7" which gives you a free mechanism to build C/C++ extensions. See https://www.stevemcmahon.com/steves-blog/building-plone-on-windows-10 for details.
I think we just need to do a better job of documenting. I'll try to do some of that myself.