I can only speak for what I used in that era: Windows 3.1, 3.11, 95 and 98.
That said, my best personal experience was with Windows 3.11. I’m sure we’ve never used the Workgroups version (which I use on my virtual machines actually) at home, my dad always got copies of non-workgroups versions only, and he still hasn’t opened his CD box of OS/2 Warp 4 to this date. Also, we didn’t have Internet until we had Windows 95 running, but I can’t say that for sure because I have memory glimpses of me using mIRC under Win 3x.
I found out that I prefer the Program Manager experience instead of the Start Menu experience (which became worse after Windows 7) . I never used the NT versions; With the move from 3.x to 9x, DOS slowly disappearing, I thought it was a good thing but looking back now, it wasn’t, because like someone said on this thread, DOS was still a needed thing in 90’s.
All in All, apart of the (terrible) Start Menu, the Windows experience did really improve with things like Device Manager. Ah, the joy of the plug-and-play era - something I would have welcomed in Windows 3.x. Did the NT versions of 3.5x had it too? I don’t know.
At school, the first computers we used were Windows 95, and the first school with computers I attended was around 1996. If I am not wrong, I was in fifth grade. Between the classes, we used to go there and play DOOM II between us.
Meanwhile at home, we went through the straight upgrade process: 95 - 98 - 2000 - Me - XP - Vista - 7. We jumped the 8 and 10, because at this time we had already moved to Apple ecosystem. Windows Me we didn’t even use really - it lasted a few good weeks until we reverted to Windows 2000, where we stayed until (arghhhh) XP.
I never really used the NT versions 3.x and 4.x, I’m sure my dad used them at some point in his work. I remember thinking that these versions were a bit more complicated to use for some reason, because (let’s remember that I was a kid back then) of the naming conventions: “NT”, “Server”, “Workstation”. For example, when 2000 came in, I never really knew that there were various flavors of Windows 2000 (Datacenter, Server...).
One curious thing is that I had never thought that the NT versions would become what Windows is now. Although 3.x and 95 were ridiculously unstable and would throw GPF and BSOD at me numerous times, they were the best OSes I ever used until I was presented to OS X Snow Leopard.
Actually, when I was at university, the computer room had macs running Tiger or Cheetah (?). I remember because the UI was Aqua. No Windows computers there for some unknown reason. I can’t remember now which iMac was there.
And two years ago when I was increasingly angry with Windows 10 changes and automatic updates, a wave of nostalgia struck me, I started doing VMs of old Windows versions and hey presto, here am I now. I’m feeling an old grumpy man now.
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