The idea that "each generation does better than the last" was a functioning social contract for decades. I think it ended with millennials.
I mean, when I look at my grandparents generation: houses cost about 3x the average salary, so they were easily affordable. Post-war manufacturing made it easier to build wealth. They had harder physical lives, fewer global goods, but high baseline security.
My parents had to finance their house at 7% interest rate, but they could still afford it. Then there was right-to-buy. Both worked rigid 9-5s and they didn't really identify with their jobs the way we are supposed to. But they were always financially stable, and they inherited from my grandparents (who they cared for, btw).
When you look at us millennials... Houses cost 8x-9x the average salary. You have the gig economy, stagnant real wages. At the other hand, our lives are "convenient" (for lack of a better word) in a way that our parents couldn't have imagined at our age. We have WFH, streaming, instant delivery... But minimal asset wealth. I don't think we will inherit anything, my MIL has Alzheimer's so she will need lots of care for many years, and I am unlikely to inherit anything from my dad since he'd remarried after my mum died.
I think the biggest difference to before is that our parents and grandparents lived in an economy where wealth was largely built through work. If you got a decent job, your salary was tightly coupled with what a house cost. Today, we live in an asset economy. House prices have skyrocketed by thousands of percent over the last fifty years, while wages completely flattened out after the 2008 financial crisis. The safety nets that used to exist are no more.
So, do we have a better lifestyle? If you measure "lifestyle" by a great childhood, streaming options and flexible working hours, yes. But if you measure it by peace of mind, disposable income after housing costs, and a clear path to retirement, our parents absolutely won that round.