I have moved way outside of the lives and experiences of everyone I know from school and my family. No one minds or holds it against me (other than possibly my SiL, but she has lots of issues, not just with me).
In my experience, it is about how you present yourself. No one is bothered about my life and what I do or don't have. I am exactly the same grumpy, down to earth curmudgeon that I have always been.
Possibly the phrase, 'they have both worked very hard for all they have' is a clue. A lot of people work very hard and due to social conditions / life, do not manage to rise out of the basics of life. My mother is one example. She has worked her fingers to the bone and is still poor. Someone saying, 'Oh but we earned it' would be galling to her because it implies that those that aren't lucky haven't worked as hard.
They are lucky is all. As am I.