(Apologies for any typos.)

Oh boy this is gonna be hard work and all from memory, I haven't seriously touched Windows for years.
(Who remembers the IBM-XT and CGA, sheesh.)
1) MS-DOS 2.1 to 6.22.
2) DOSSHELL.
3) Windows 2.4x to 3.11/WFWG.
4) Windows 95, 98, ME, 2000, XP, Vista, 7, 8-8.1 and now 10 with SOOO many variations on any theme with a proportional price tag.
5) FAT, VFAT and NTFS, (did WinFS ever make it?).
6) INT 21
7) EMS, XMS, UMB, Enable A20 line for an extra 65520 bytes above the 1MB boundary.
8) Real Mode, Standard Mode and Enhanced Modes to current CPU type modes.
9) DOS Extenders.
10) Having to install any new proprietary hardware with supplied drivers. This could end up being a nightmare.
11) And finally MS-Xenix, who remembers that then.

Well contrary to belief Windows 3.00A would install in Real Mode and used DOSSHELL's swapping techniques instead of a swapfile.
There was a file, can't remember which one now, in Windows 3.00A that would allow Windows 3.1x to also work in Real Mode although the same filename in the 3.1x set the minimum of Standard Mode for 80286s, boy did I love hacking.

LIM standards were set up for _memory_management_ and had to work Lotus/Intel/Microsoft's way.

Bloatware slowly became a new buzzword around the Windows environment, however......

There are some seriously professional software tools for this environment and only a very few have reached the *NIX desktop.
MS-OFFICE is pretty much de-facto for the small works office suite and is available for Apple, dunno about *NIX flavours.
Photoshop is well, what can I say, it has its own worldwide buzzword 'photoshopped', says it all really.
Directory Opus, stolen from the AMIGA days, probably one of the best file managers around for any platform. I would love it on my Apple/Linux Mint machines.
As for top notch electronics and engineering CAD stuff, most are not even available for *NIX/Linux.
Windows is usually de-facto for a top notch games machine, although Linux is now becoming recognised by Graphics Card manufacturers.

My first taste of Linux was YGGDRASIL Fall 1995 edition, I never ever got it working. Still got the original two CD disks manual and box.
This put me off until Caldera ? and the sound would not work unless I booted into MS-DOS and run an MS-DOS program to set it up and relied on LoadLin.exe IIRC to start Caldera; one too many MS-DOS inputs put paid to that.
Mandrake 9.0 was my next and actually worked, for a while, then the graphics went to 16 colours instead of 16 bit depth and I couldn't solve that either; goodbye Mandrake, Linux was not quite ready for consumption.

My next was Debian 6.0 around 2011, oh boy this was a revelation, LINUX HAD FINALLY ARRIVED AND COME OF AGE.
This was probably the single most stable OS I have ever encountered and I installed PCLinuxOS 2009 alongside it and was also extremely stable.
Both did exactly what they said on the tin, Debain was more professional and PCLinuxOS was more user/consumer friendly.

There are a plethora of professional level tools to suit everybody nowadays and most are GPL'ed, GIMP for example, but those who have used Photoshop moan about its interface. Sadly however they don't quite match the commercial/professional tools that exist for Windows.
Unlike Windows the *NIX command line and terminal along with its tool chain is a force to be reckoned with, this is probably why MS are building BASH into their environment and I am speculating here all the tools that go along with the shell...

I now run as my second OS Linux Mint 19. This is as solid as a rock, probably more so than my current Apple laptop.

I hope I haven't bored you all too much...


;oD