No you don't, or at least I don't. I need secure software. Frequent security upgrades are a good indicator that vendor didn't do a good job at the start. Once in a while, ok, and debian supports a special channel for security upgrades for this very purpose.
I do agree that with perfect software, written by perfect developers, updates aren't needed. I mean, has anyone ever had to "update" the Mona Lisa? I hold my web browser to the same standard.
I don't get the contradiction. Are you implying that security update don't 'just work' or that Debian doesn't push security update?
The kind of 'just works' that most refer to is that they turn their computer on and start working, rather than turning their computer on, being forced to login to a net account, being forced into a tutorial dialogue for a newly added feature, and then realizing that BigCo deprecated your file format support last forced update because they replaced it with TheNewWay.