system
A chat on subreddit /r/pcmasterrace
human
95 was a head and shoulders evolution over 3.1. It faster, better, and more capable in every way. 

98 and ME were the “OS mom got on the prebuilt at Circuit City” upgrades. Anyone who did it themselves went 95 —&gt; 2000/NT —&gt; XP —&gt;7 —&gt; 10. 

But OS lifecycles are long enough now you’ll likely have trouble holding out until windows 12.
gpt
Mmm, that's not how I recall it. Windows 98 (especially SE) was a pretty popular upgrade, it was only ME that got universally trashed and avoided.

Also prior to XP there were two different Windows kernels/tracks. NT and 2000 were based on the NT kernel and targeted towards the business environment, while 95/98/ME were DOS-based and targeted towards home users. Home PC's typically went Win 3.1 -&gt; 95 -&gt; 98 -&gt; XP while work computers went Win 3.11 for Workgroups -&gt; NT -&gt; 2000 -&gt; XP. Machines going from 95 to 2000 were pretty rare.