Because undiscovered security holes in operating systems are so common, using any outdated OS quickly becomes like driving a Ford Pinto. Maybe you think your Pi

Because undiscovered security holes in operating systems are so common, using any outdated OS quickly becomes like driving a Ford Pinto. Maybe you think your Pinto is "good enough", but taking it out on the road is dangerous to you and others. The stigma of using an unpatched operating system doesn't come from anywhere irrational as some stigmas do. It is like the stigma of having poor hygiene. Pooping out in the open in your back yard has serious negative health repercussions. That is a much better analogy than the "classic car" one.