Yes!
The plan is to have 5.2.2/Python 2.7/3.6-3.8 ready for Windows. Thus said, the buildout.coredev 5.2 branch already works on Windows again with one manual step. I described the process here:
The installer was also fixed (for next 5.2.2. release), also there were fixes in plone.recipe.zope2instance (but one big issue pending here, workaround available - see my referenced posting above) and also in plone.recipe.zeoserver. I also introduced workflows for Github Actions to at least do some basic automated checks on windows. I fixed z3c.jbot to work on Windows. Most of the changes are merged but unreleased for now, so the git branches must be used to make it work.
So we made good progress - that said any help and real world testing would help to get this more polished.
With all this developing for Plone with buildout.coredev works fine. For production I would wait for the 5.2.2 release.
We really need more people helping with Windows issues. While porting Plone to Python 3 we had MacOS and Linux people on board, but nobody developing on Windows. I have to admit, Windows support was not on focus. Also our CI worked at the time on Linux only. Now this falls back on us.
Any help is here highly appreciated!
If you can not wait, Plone works fine in the Windows Linux Subsystem:
https://docs.plone.org/manage/installing/installation_windows10_wsl.html