I think there's an obvious and more general question here to be answered: if a piece of software is good enough, namely, it "disappears" when you are trying to do your job, then why bother to change it? Yes, the new version might enable a more efficient workflow, or might be faster to boot-up. But people hate changes and you need to invest considerable time in upgrading a piece of software (the upgrade itself + learn…
Interesting, readers of HN should know that upgrades to the newest version of Windows and updates is essential for reasons of software security. Newer versions of Windows incorporates security measures not in older versions -- sometimes even taking advantages of new security features in Intel hardware. For example, Target and Home Depot were hacked because they failed to upgrade their point-of-sale hardware from Wind…
I've worked with people very used to working with enormously complex systems and even they say Walmart etc is on the higher end of that scale. We're talking weeks of people on site to get new software stood up.
This isn't to diminish your point about the need for upgrades, but it's nothing like a push button process.