I think for a lot of us, if I have a perfectly working car, why would I use my time walking (or driving

) to the car dealers in the first place?
There is a time cost in updating, and a risk. I just updated my phone to Android 5.1, I pressed "OK" and came back half an hour later, all complete and working fine. It could have all messed up, in which case I would probably be looking at a factory reset and an hour out of my life reinstalling stuff.
For me, Windows has always been a pain to install, and risky to the point that I have always installed onto a fresh hard drive or SSD so I can just plug the old one back in. So that adds the cost of a new SSD or hard drive.
For me the upgrade from XP to 7 was worth it, because games were starting to expect to be on 64 bit and graphics cards were getting too big to use in a machine that can only address 4GB in total. I am not feeling that push from 7 to 10 yet. I never felt any push/pull from 7 to 8, and I even went as far as buying the cheap license deal they did at the start of that just never used it!