The only actual _windows_ problem of those you listed is that uninstalling software is a hassle. That said, it isn't a walk in the park on Mac either.
Can't use Emacs on Windows? Use any other editor.
Can't setup VM in VirtualBox? A VirtualBox (maybe) problem
If you go on Windows expecting the same environment as OSX or whatever OS you're on, you're going to have a bad time. Booting up a fresh Debian install feels better because you know what to do already.
Booting up a fresh Debian install for anyone else is likely to be an almost impossible undertaking without reading some kind of guide, if you're wanting to setup a proper dev environment.
There are problems in any platform you chose, you're probably just subconsciously sidestepping those in your process of setting up, while the Windows ones stick out to you.
Example problems I notice on Mac that are fine on Windows;
Docker is extremely slow, I need to run it inside a Linux VM for any kind of proper developing
Window management is horrible
Installing software
Now, I'm no advocate for any OS, I love running Arch Linux with i3wm, I love OSX and I love Windows. I don't see any reason at all to hate any OS, I can setup my dev environment on practically any platform I could want with little or no difference. The only things that change are the things around my environment, the simplicity of i3wm, the task bar on OSX etc.
In my opinion Linux is the outlier here, which provides the greatest change in environment, not a bad one mind you, just a difference. Mac and Windows are mostly interchangable, I can switch betweem them with little overhead.