Despite my DC's privileges they have both grown up to very much empathise. DS has been doing voluntary work with Mind and DD volunteers at a charity for Downs Syndrome children.
They are both teaching, ds in academia and dd secondary English at an SEN school, often working with very challenged children and families.
The difference between us and the dc? The DC have genuine wealth behind them and therefore could chose vocations that would never pay despite being equipped for careers in Law, Accountancy or Banking. Also, they keep very stum at work about what they have.
DH and I are very aware of how hard things are nowadays. We were born at a different time when property was more affordable admittedly but over the years as far back as when I was single, friends told me I was mad and stupid to invest in property and leave dinner parties at 10pm because I had to be in work at 7.30am. So many times I was told I was wasting my life because I wouldn't pack it in and backpack Thailand and Australia. The same friends turned quite chippy when we had babies and I could give up work and they couldn't, we could afford to buy bigger and stay in London and they couldn't. So many whinges about "you are just so lucky". Er no, I didn't houseshare until 25, break up with a boyfriend and piss off to Australia for two years.
Similarly, in the playground "oh, your DH is never here to participate, I wouldn't put up with that", etc, etc. And then when we pulled ds out for independent, despite all the whinges about the school "oh you're so lucky, we just don't have that choice". A silent, well you do love, you could go back to work instead of lunches and tennis club, from me. Or "oh Jack and I would never do that, it would compromise our principles". Well good for you, lucky we don't have your principles. The couple with principles funnily enough didn't work, despite living a very mc lifestyle. I can only assume their principles were funded by inherited wealth.
In short, I do think it's about more than luck, it's also about making the right choices and a shed load of self-discipline. I don't think all wealthy people fail to empathise at all or aren't in touch with reality. I do however think there are many, many people from all parts of society who lack a decent filter.