DOS - > Windows 98 was a real value proposition and worth it I was very glad with the upgrade.

98 - > XP was also a very good upgrade that I voluntarily took with good feelings all around.

XP - >Vista was the biggest ball kick I ever experienced because I trusted Microsoft so far. It was also when I found out about Linux for the first time. I just went back to XP instead.

XP to windows 7 was a real downgrade but I was forced to update because XP legitimately got attacked all the time with malware.

Windows 7 - > 8 I didn't even attempt. Windows 7 - > 10 was only done because long term support ended. Windows 10 was a significant downgrade and it's the first time I moved some of my systems (home server) to Linux.

I'm now moving my daily driver to Linux as well because there's no way I will go to windows 11 ever. The next one after seems like an even bigger abomination.

Honestly moving from XP to Windows7 was already a humiliation ritual I shouldn't have done and just jumped to Linux and just not bother with gaming anymore.