I never had 95, my family couldn't afford a PC back then. But getting out families first PC running Windows ME and spending so many afternoons trying to fix it is that got me into IT support.
Moving to Windows XP was a huge step up and moving to Windows 7 was another step up.
Microsoft has never ever made an OS as good as Windows 7.
7 and XP are equal until in XP you try to drag a full screen window and cannot.
I'm on 10 LTSC IoT and I think (Thanks to people on the Linux sub) I'll be moving to Linux mint Cinnamon.