i too, of course, used windows back in the day, from win 3.0 and 3.11 'for workgroups' on the original ibm 'at' and a highscreen one, up to windows xp. mostly because there were no other gui os for my homebuilt pc's at that time. ok except os/2 warp and beos, i think.
after xp i quit using windows and switched entirely to gnu/linux and never looked back. when i read the horror stories about win8+, i think i did 'the right thing'.
btw. win nt4 was the best win for me i ever had contact with. it was clean gui-wise, releatively bugfree, fast etc.
windows millenium edition was the worst. install it run it some days, reinstall it, aargh!
for supporting the parents computers i have the same experience, windows had to be reeinstalled a lot, with linux it just works, for ever.
currently my mom uses a custom cutdown awesome wm with her basic programs exposed and she's quite happy with it for a long time now. it doesn't get any better i think when one also
wants security for the parents computers, read no android tablet, and, of course, no apple too.