I had kept my Macs at 10.6 for a long time but had to "upgrade" one of them to help my daughter with an iPhone problem (really annoying that you have to update your Mac just to copy files to a phone, but whatever). Everything was worse. Search was terrible. Mail was in the crapper. The weirdest shock was when I was using Apple apps and discovered they'd changed Shift-Command-S from "Save As" to "Duplicate." That move is really emblematic of Apple's direction with the Mac — arbitrary changes that either eliminate features or make everyday workflow more cumbersome.
I bought my first Mac in 1989. I bought my first non-Mac PC in 2015 and stopped using Mac altogether.