I did not know this, thanks for letting me know!
> I update aggressively on my own projects to stay on top of changes and keep the effort related to mitigating compatibility issues at a minimum. A nice side effect is that you get all the latest security, performance, and other fixes. In my experience, updates get harder the further you fall behind.
This is absolutely a best practice, though I think people struggle with it for all sorts of reasons. In general one of the downsides of maintaining a diverse codebase is that this constant update cycle becomes more and more difficult, and it's one of the things that I find drives towards more consistent tooling within a team.
> I work with a lot of customers running ancient versions of whatever for no other reason than that they seem a combination of fearful, ignorant, and indifferent about what will break because they can't be bothered to even try.
While I agree this is something people need to get over, we have to take some blame for this as an industry. A lot of people have bad experiences with upstream Shiny Object Syndrome.