I can’t say personally, but I have been on this list since the very early days, when it was an actual mailing list (even before Google Groups, and certainly before Discourse). In that time, I can honestly say that the amount of signal/noise around Windows has been very very tipped toward Basic System Thing Doesn’t Work As Expected, and away from even Gem Won’t Compile, or Code Won’t Run. The problems seem to be foundational in nature, and getting over them just means that now you’ve graduated to the next level of difficulty.
I have seen people with far more experience in Windows than me (I mean, you would have a hard time having less Windows experience than me if you had never walked through a Best Buy in your life) try very patiently to help someone get things working at all, and often, the final message in the thread has been something along the lines of “get VirtualBox running, and install Ubuntu”.
In 2012, I taught at a weekend RailsGirls bootcamp, and we had a very slick installer for Windows called RailsInstaller or something like that. It worked about 70% of the time, and was truly magical for those people, but for those who couldn’t make it work, it was a very frustrating process with a lot of back-and-forthing, and some of those women were only able to watch over someone else’s shoulder while they did the classwork.
I am certain that it’s better now with the Linux subsystem, but how much better? Usable? Maybe the lack of complaints more recently are a sign that the worst is behind us. But I would tend to doubt it, if only because my memory is so long.