Now when Win. 8 is nearing EOL - do you have good or bad experience with using outdated version of MS Windows ?

I don't know quite which box to check because of several factors. I have gone for 13 months twice without ever booting any Windows on any PC but since when I do need Windows for something like initial hardware support, like some BIOS image extraction or setting a default on a peripheral, it makes me mad that Win7 is not only not supported but actively sabotaged (specifically with USB) in order to force users to move to that abominable Win10 EULA.

Now I just keep a Win7 install on an older chipset PC for the rare moments I need Windows and WINE won't suffice.

'No experience' - I haven't had MS on any of my computers since 1999, apart from new ones, which had it replaced with Linux within the first 20 minutes of ownership.

Windows 98 SE was actually all right.
Then XP SP2 was ok and still occasionally seen in a shop with grease monkeys... just works with an even older oki dot printer and is never connected to the web.
Whole schools running win2K Pro with 128M of memory, those were the days. Now I think Win10 minimum is 2G but real world is double or quadruple that.

I you have both good and bad experiences you can choose that which is more intense.

These sabotages are well known and make my aversion to Win. stronger and stronger.

I use Win. only when necessary, few times in a year. I never use outdated Win. for access to internet because I don't believe it's security

Congratulations, you have saved big amount of time, energy and maybe hardware

Yes I remember win2K Pro with 128M of memory at school

No experience because I havent used windoze for 13 years. The last one I used was Vista.

Unfortunately, "modern" versions of Windows are "ridiculously fat." They require a very capacious computer just to run at all, and they soak up much of that capacity with unwanted and undocumented "extras." (It's also disturbing to see just how much the software is now spying on you. "All the things you see it's running" are mostly not things that you asked for, but you can't turn them off. Somebody in their Marketing Department thought they were "kewel," and now you're stuck with them.)

Older versions of Windows still run much cleaner, but Microsoft has completely abandoned them. They won't update the TLS certificates anymore, so eventually websites will stop allowing you to visit. If you still need something that still needs an older version of Windows, Microsoft simply doesn't care about you.

I have particular hardware or virtual machines to give me the Windows level support that some of my clients still need, but for everyday purposes I am always running either MacOS on my MacBook Pro, or Linux on everything else. For one thing, it is simply so much cleaner and faster. If you're just looking for a computer to do everyday things with, such as running your surfboard, then you simply don't need Windows and all the headaches that now run with it. Linux can do the exact same things much(!) better now.

Windows 7 Virtual Machine works the one use I've needed windows for; my harmony remote.

XP and Windows 7 (in VirtualBox) keep my Printers/Scanners alive.
I keep the Manufacture's original drivers though, do not install anything from the web.

I remember really enjoying Windows 98. It was easy to use and ran quite fast on the hardware of those times. I can't judge XP because I was put off it by the cartoonish interface. That was why I started using Linux.

No problems here with Windows 7. Need a replacement for Ms Security Essentials, though...

Plan is to roll back to one of the first, trimmed installs and take it off-line. Only to be bootet for my photography projects. Have a nice workflow with a collection of old Windows-only tools, so... have to.

A second install is needed for online racing and as that is bootet as a stand-alone disc, I don't have to care about virus, hacks and-what-not. By all means, destroy it! The backup can be fully restored in less that 10 minutes...

Outdated? My entire Windows software collection is more than 10 years "out-of-date", but gets the jobs done.

That's where my Microsoft history ends after +30 years. We have to split as we can't agree on who owns the pc...

Linux? Nice to be in command! And Slackware is a breeze...

I still use a pc with windows 7 and it works fine. It lacks some desktop utilities but I can live with that.

I keep a laptop with windows 98 but can't bring myself to start it up. I even played Age of Empires on it back in the day.

Have Win 7, XP in VMs. Neither has access to the internet when running ... So good experience. XP hasn't been started in years but is present, Win 7 occasionally gets called up as my wife likes Print Shop for some of her projects. Anyway the VM environment is the best place for these OSs.