I upgrade software regularly. It has become easier to do so with each passing year. Early on I had to plan for it, reach out to repositories, etc. Nowadays the software will usually prompt me.
Many folk don't like software updates, because the cost in convenience can be high. Even subtle changes in user interface can break many unarticulated means of working. The benefits are often hard to perceive: new features that you didn't know that you wanted.
The main reason that I regularly update is the benefit people don't like to think about: increased security. Everyday a large number of people spend their day trying to break into other people's computing technology. I saw this up and close when I hosted my own web server; I'd say the main reason I stopped at the end was the required vigilance as literally thousands of entities tried to break in each day.
From my casual perusal of security blogs it seems as if the majority of break-ins occur because folk have not updated their software because of the inconvenience. Newer versions of software are inevitably more secure. The image that comes to my mind is that of someone too lazy to lock their front door in an area prone to burglaries.
Operating system upgrades have a larger cost, hours of lost productivity during the reboot and the subsequent shakedown period. The need for improved security is much greater there.
My father taught me to respect my tools in order to get the best performance possible out of them. I don't do woodwork but I still follow in his footsteps.
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