There are two separate issues: consumer goods and actual well being. I think you overestimate the difference in consumer goods between the ruling elite in the Fifties and the contemporary welfare underclass: the latter rarely, if ever, can take advantage of commercial air travel and have severely limited access to open-heart surgery. And barrier birth control and abortion were readily available (albeit significantly more expensive) to the rich in the 1950s, while in the modern day they (especially abortion) are somewhat difficult, though far from impossible, for the underclass to access.
But quibbling over those details can make us ignore the more central point. Access to consumer goods is only part of the picture, because power is a very strong and often superior substitute good for most of them. Roombas are accessible to the middle class today, but they are inferior to an actual person cleaning the house for you, even with an antiquated vacuum cleaner from midcentury. The vast majority of the population can text each other now, but a well-off member of management could very easily have a secretary do the same through a messenger boy. The latter is slower, but in some ways easier: he (invariably a he) had at will access to an intelligence superior to the most advanced AI now, without the burden of having to hit tiny keys, save phone numbers, or remember to charge his phone. A member of the upper class in the 1950's did not have to worry about employment; about housing; about having interesting work; about getting fired for drinking on the job (hell, your company would pay for your booze and cigarettes); about worrying how to pay the bills the next month; about sending your kids to a school with regular shootings; about visiting the social worker to prove you had sent out pro-forma applications to jobs you're incapable of performing so you can get your welfare check.
Some tradeoffs are less clear. The middle manager in 1955 had to worry about global thermonuclear war, but not about catastrophic climate change or poisoned soy sauce from China. We have hormonal birth control, but also HIV.
All of us are members of the professional upper middle class, so we're certainly better off. But an unemployed single parent living on the bad side of Hunter's Point? If I were forced to choose, yeah, I'd definitely go with the rich straight white guy in the 1950s with massive social privileges. Even with fewer gadgets and less sophisticated technology.
And frankly, the poor have much better access to health care thank you think. I know from personal experience that a poor, uninsured person can still get necessary or even largely elective surgeries that may not have even existed, and surely would not be performed with the same level of safety and quality, in 1950.
Oh yes--and abortion was actually illegal in the 1950's.
You only have to go back to the year 2000 to give up iPhones. Going back to 1990 you give up the Internet. Going back to 1980 you give up Mac and Windows. Going back to 1970 you give up microwave ovens and personal computers at all along with cable television. Going back to 1950 you give up birth control, open-heart surgery, commercial air travel, and color television.
That's just technology. There's a huge cultural gap, too. In 1950 segregation was the law, there was little to no access to foreign culture, atheism was distrusted and associated with Communism, pre-marital sex was taboo, and women by and large did not work outside of the household, especially not when they had children. None of the music that I listen to even existed back then. None of it would even be possible.