I work with ....wait a sec, let me count..... 8 separate computers daily and a couple others on a semi weekly basis for people with questions. Everything from 1 with WinME up to Win8. Have 2 at work that are stuck with XP into the foreseeable future since they require a 32 bit OS to operate specific peripherals. One runs an engraver (directly with a serial cable) and the other a specific embroidery software. Both have (several) thousands of files that would be lost if we had to upgrade.
I cut the internet connections on both of those XP computers a few years ago and DO NOT add anything un-needed to the systems. They work as is and just keep hoping the power supply does not crap out. I have 2 fall back XP based computers stashed away in the basement if (when) they fail. Make lots of back-ups.
Of all the different operating systems... Win8 would be my choice! After getting used to it, i prefer it by far. Front end, i can arrange my program tiles on the new "Start" screen with all my important programs but they can still stay hidden and show at touch of a button. Would sure think many of you "smart phone" users would like the App style layout. Under the hood, have hardly had ANY crash or freeze issues EVER with the newer programs made to run on Win8. Running 3 separate systems with Win8 and they all run a lot more smoothly than any of the others.
Consider myself fairly computer literate, but on the first system we upgraded to Win8....... i had to do an internet search just to learn HOW TO SHUT DOWN the machine! No joke! There is some learning to do, but change is good.
Windows 3.1? Can still remember playing the
Mail Order Monster video game on my Commodore 64.