Windows 95 and 98 generally feel like a mess overall. The stability issues made the OS;s feel like a mess in comparison to modern systems who can mostly handle most types of hardware and hardware changes seamlessly.

Windows 2000 probably shouldn't be included since that OS wasn't really dedicated to consumers, or if it's included then other NT versions of windows up to that should also be considered.

I seriously do like Windows XP and it's overall look. Significantly more stable than previous 9x based versions of Windows. It was perfect for it's time.

Windows Vista despite all it's initially deserved hate did become a good OS but never managed to gain traction due to the bad reputation it had gained initially. To be fair the development of Vista was also troubled too, needing a full wipe like halfway through it's development cycle before becoming what it is today.

Windows 7 is just Vista rebranded for the most part. I do still really like the OS and it is the one I spend a good chunk of my childhood using. But it's interesting to see how it completely overshadowed Vista despite at the core and even visually in many ways being similar to Vista.

Windows 8/8.1: runs ok, but the UI is a complete mess. Forcing desktop users to use a tablet interface for the start instead of the original one was just a mistake. I'm somewhat surprised everyone just A-OK'd all of this and didn't stop to think whether it would be a good thing. The best approach would be what they have done in Windows 10 with tablet and desktop modes. This is also where tracking and privacy bullshitery started creeping in.

Windows 10: good OS overall but could be better. Even a worse tracking and privacy wise compared to previous versions of Windows, maybe going enterprise could help but idk. Lots of advertising and the biggest annoyance is the mess of UI's. They started transitioning a lot of the UI element to the newer W8/W10 style but never finished it. So now you have the old control panel and new settings app and I find myself always having to go to in control panel options to adjust sounds, uninstall apps etc. while the new settings app and it's options are just an impedance to me and all the things I do. I hate it when I type sounds in the search bar and the settings app option shows first which doesn't have any of the settings I need such as adjusting volume of the mic, amplifier, disabling/enabling devices, etc. It just annoys me. If you're going to do something at least do it properly. Not to mention the bloat that comes with a fresh windows installation. NO MICROSOFT FOR THE THOUSANDTH TIME I DON'T WANT TO PLAY CANDY CRUSH ON MY GAMING PC STOP INSTALLING IT EVERY TIME I INSTALL WINDOWS.

Personally if I could today, I'd still be running Windows 7 on all of my machines, no stupid bloatware, no mess of UI's. Just a simple functional OS that does everything I want it to.