I’ve liked each increment of the path I chose at home: 95 -> XP -> 7 (small dabble in 98). Can’t see going to 10. May end up leaving my 7 machines for offline activities and go to a Unix-based system next.
My Windows 7 needed repairing so I broke down and went with a new 10 for maybe 5 days. Pure h e double hockey sticks. Fixed my old 7 and am happy as a clam... if only it’d play my old 98 and XP games.