well psycosmyth if you try to make improvements you have to take chances and sometimes it won't work out but you learned (hopefuilly most people do) something and therefore you already improved. The question or the way how to see it is quite philosophical I admit.
For software updates I'm in so far update "addicted" as long as security is concerned! For the rest well as long as it works and there is nothing added which may be interesting to work with I usually like to stay with the one I got (Never change a running system
I do agree that some people can't really value what they have and never take a breath to see what has been accomplished or even to take a step back and see what the urge to get more and more independent on technology is doing to humanty. But then if you lean back and see what is going in the world you quickly realize a lot of madness there... but I'm getting off topic, sry...