Mark Pilgrim is happy after using Linux for a year, because he finds that automatically updating software on his computer is surprisingly painless:
Each Linux distribution has now automated basically everything about [package management] that can be automated – everything from worldwide mirrored and load-balanced distribution servers to filename and pathname standards to developer tools for the packagers themselves. I recognized years ago that "the fanatical devotion of the Debian package maintainers makes the difference." That's still true: they're still fanatical about package management, and it still makes the difference.
By comparison, he notes, his Macs are more difficult to update. System updates are automated via Apple's built-in software updater, but all other applications have to manually updated in a variety of different ways.
I would probably find the same thing on my Mac, but unlike Mark, I'm not really obsessive about updating all the software on my system. While most software I use releases updates fairly regularly, I don't actually care enough to install the updates.
What's the risk if my text editor isn't as up-to-date as it could be? That's not going to affect the security of my laptop. Even applications which connect directly to the internet, like my feed reader, use the built-in components like WebKit. These are updated by the automatic system updates, so I don't need to be too concerned about strictly updating these applications either. My IDE, my Office applications, the few games I play, none of these applications need to be updated.
What I do update regularly are my web browser (Firefox, automatic), operating system componenets (automatic), and the network services I have enabled (SSH, HTTP, SMB, iTunes, also all automatic). These updates cause me no pain, other than an occasional system restart.
Mark mentions that he has 902 packages installed on his Linux system. On my Mac, which I use both inside and outside the office, I have maybe 10 applications which I installed and use regularly. Package management and automatic updates for those 10 applications simply isn't a problem. I don't understand why it would be for Mark's wife or his parents either.