I think you didn't understand the problem. Not the "Updating your machine" is the problem - the problem is that new versions of applications tend to introduce new bugs (or trigger old ones). Just think about the headache pulseaudio caused. The problem of Linux software management is that if I want a new version of e.g. pidgin, because it supports a new protocol, I need to upgrade the whole distribution, which will install pulseaudio (among other stuff), so I won't have sound. This happens even when I had absolutely no intention of going anywhere near pulseaudio.
The hardcore Linux-advocate's answer would be that in this case grab the code, compile and install, but it's definitely not as easy as clicking "Next -> Next -> Finish" and then the advantage of package management is lost (no automatic security fixes, no warning if a used library gets updated with some incomtaible code, etc.). The Windows solution might be uglier on the inside, might contain lots of duplicated libraries installed - but works, and that's what the user cares. Of course, until the FOSS developers treat their users as beta-testers, then noone should care about things like this, but this road doesn't lead to world domination.
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