Or a philosophical one? What is it more proper to grieve over?

I don’t have a philosophical answer to that. It is proper to grieve for anyone who dies. The hierarchy is a psychological question. Is it more proper to grieve for someone close to you or someone distant? In my view, there is no philosophical or halakhic hierarchy. Psychologically, people usually grieve more for someone close to them (and that is why Jewish law also responds that way).

And what about the heart-rending descriptions that always appear? When it’s a father of a family, they say it’s especially sad because he has a family; when he has no family, it’s sad because he doesn’t have a family; when his life was good until the very end, it’s sad that such a life was cut short; and when he suffered, it’s sad because he suffered even before he died. Is there some scale of hierarchy that is more “correct”?

As I already said, I’m not dealing here with psychology. As for having a family, here there is an objective measure: when he dies, the family suffers.