I've been using this for months.

Isn't Cygwin Linux-flavored Windows? I was assuming this was running Linux in a VM or something, where Cygwin appears to just be a CLI that looks like Linux with Windows equivalents of the most basic Linux applications. Y/N?

Hmmm.
Since I started university I got interested in linux and after a while I doodled round with a distro, I think it was eventually arch.
However the unit I was working on well its old and its battery went flat, it was an old xp unit and when I returned to it to continue after a few weeks it just didn't work anymore so I reformatted and put xp back on it.
At the time I was fiddling round I was really sick and unable to do much of anything bar type, I don't really have that sort of time as such to really handle it.
I did fiddle with wsl a bit but yeah the package manager if you update it enough does well screw it up totally and eventually I was able to get the commands to completely clear its packages.
Cygwin, I tried ages ago, but I really didn't care about its setup, if there was a way to install all its modules or bits in some sort of downloadable innosetup script or something maybe but to be honest I never got the interface to work right at all.
My next plan was to retire this old 5 year old toshiba and once I get a newer hp load sonnar, yeah I know its the cheap way out but unlike other distros based on arch it can be updated for ever in a day without an image on the other people have been going on about ubuntu mate which uses above all things the old gnome 2 environment though it may be on its last legs which I was happy using back in my old university days.
On the other hand I am unsure still on this reguard my other idea was to vm it and eventually buy a box where I could happily set it up log in etc and it would just work.
Ofcause my main put off is that linux readers, ie orca are not as accessible as windows screen readers like nvda.
In your opinion is it worth if at all possible trying native linux again if I have a system spair, actually I have no doubt its the best, but is it worth running vmware or something on say a laptop or system with hardware vertualisation I know without it its complete rubbish or is cygwin fine for what I want and is it worth using it.

@ironcross32, you can pretty much do the same thing with Cygwin. The interface for the installer can be tricky to use, but I've managed to get it to install all the modules. It's over 100 GB so yeah.

I just have a vm running that I ssh into. It does fine.

Cygwin is a pile. WSL is probably a pile. Both are still 25 times better than trying to run a Windows port of whatever Linux application locally. Ask anyone who's ever tried to set up a MUD/MOO server. If you can't afford a license for VMware, or don't have the resources to run it, it's still the better option. Me personally, I prefer a $20 VPS. but I'm not above installing something like this for a local dev environment, because let's be real here. Windows to Linux compatibility is a bitch.

I do also have a VPS, and yes, I can say winmoo is a fucking pile of dumpster turds on fire with rabbit piss sprinkled on top.

The Windows Subsystem for Linux is not intended for that. I'm not aware of any way to install Orca, but even if there was, you couldn't get it to work as the subsystem does not have any way to play audio. You probably don't need it anyway, it's a command line and that should be accessible to any screen reader.

If you want to install Kali, just search for it in the Microsoft store and run it when it's installed. The setup process is fully accessible.

i've already did it, i was meaning for the Kali distro itself.

Hi,
I just wanted to clarify things which showed up upon the first posts in this topic, regarding the difference between Cygwin and WSL.
If it comes to Cygwin, you are depending on some comparably unstable environment. Cygwin integrates quite heavily into your system (registry, a veeery large installation if you don't know how to prevent it from installing all the stuff you don't actually need), the launch time can be quite bad if there are many tools installed. Its advantage is that things like X do work quite well, but thats almost it. Cygwin only knows the Windows filesystem and is limited to that.
WSL isn't some Linux emulation, cannot be compared to VMs or whatever. WSL is an absolutely real Linux distribution, with a layer underneath which maps linux-related hardware stuff to their equivalent Windows counterparts. It doesn't yet know all the required Linux stuff, but it improves from Windows 10 upgrade to upgrade. That means that you can just use apt-get to do all the stuff like the real Linux distros can do, a thing cygwin doesn't yet know. There are helping hands like cyg-apt or apt-cyg which try to simulate an apt-get command for cygwin, but the don't really work at all. Also, repairing a broken WSL isn't any kind of problem, compared to repairing a broken cygwin environment. Its simply deleting the old linux distro, re-downloading it and installing it. Done.
The WSL also has some positive impacts on Windows 10 itself. The default notepad application from Windows 10 will know Windows and Unix line endings from Windows 10 1810 onwards, WSL can run Linux commands as well as Windows commands, which allows you to write sh scripts which combine the full force of Linux and Windows command line tools alike, without the need to compile some special stuff for Cygwin first instead of simply running apt-get for it or maybe even download a pre-compiled linux binary from the net.
Since Windows 1803 Linux daemons even continue running when closing the bash window, enabling you to run e.g. an ssh server on Windows machine, even though you can just use the WSL when connecting to it, but whatever. It almost replaced my Debian VM already, and it reduces the VM overhead regarding speed and performance drastically due to additional apps like VMWare Player, QEmu or Virtualbox no longer required to launch it.
Its not yet worth using in production environments and it still needs many improvements to fully integrate into the Windows environment, but its deffinetily a step into the right direction by Microsoft, they finally noticed that Linux actually is a thing for developers and native support for it is just amazing. I also like the idea more to have a distro running which gets developed by a community which can rely on a much larger user base than Cygwin has to offer.
People who are happy with Cygwin can stick with it for sure and as long as you don't have Windows 10 running you probably have no other choice than taking a VM as an alternative. But as soon as you got Windows 10 flying around, give WSL with e.g. Ubuntu a chance. Its faster, more elegant, an actually real linux and its not as easy to break as Cygwin is .
Best Regards.
Hijacker