I've managed to get Plone up and running on Windows:
Install Scoop (it's like homebrew/apt-get for windows)
In powershell (not cmd) I run the following:
iex (new-object net.webclient).downloadstring('https://get.scoop.sh')
scoop install 7zip coreutils curl git grep openssh sed wget vim grep git-with-openssh rsync
Then, just for vanity, I change the powershell theme
scoop install concfg
concfg import solarized small
scoop install pshazz
To use Python2.7 I need to add a new repository (they call a repo a bucket)
scoop bucket add versions
scoop install python27
After that I install Plone.
There is a collection of tools called gow (I think that stands for gnu on windows), this ships with a putty based version ssh (you DON'T WANT that, you definitely want git-with-openssh), the ssh provided by gow irequires the use of special putty ppk keys. You'll need to generate your special ppk using puttygen, lots of not fun steps. This also affects things like rsync which I still haven't gotten to work reliably.
If you insist on using putty's ssh then you'll need to become familiar with pageant, which you can run in a separate shell window.
Once pageant is running you can ssh into sites against the putty ppk key.
If you get error:
ImportError: No module named pywintypes
pip install pypiwin32
That's all for now.
When I did finally got Plone built it took forever to start.
Next I'm going to explore Steve McMahon's approach, using Microsoft's visual C++ compiler for Python 2.7