I made the first post on this subject last year. 
"There is one issue I have with automation that no one ever talks about: 'What happens when the lights go out?' What happens if the cost of fuel gets too high to fuel the machines? Yes, there will be new technologies for energy, but will they be destroyed like Tesla's Tower when there's no money to be made from it? What happens when human beings get so far away from knowing how to take care of themselves without the machines that they cannot survive without them?"
First question: When the lights go out, those who know how to make the lights go back on step in and provide the service. There will always be a profit motive to do so, and those requiring the service will almost invariably have something to offer in return. Remember that this includes barter and even companionship.
Second question: New technologies are never destroyed because they become cheaper. What happens as prices decline is that as the price of a good drops, downward pressure is created on firms' incentive to produce. The profit motive decreases (and/or firms begin failing under the pressure) and this pressure causes supply to drop accordingly as capital expenditures begin to decline. Either some market actor will find a way for the good or service to be made cheaper, and therefore profitably at the lower price, or supply will fall until such point that the price begins to rise. When profitability is seen again, capital will begin entering this market again, and any disruptions to supply will be restored. Without the coercion of the state (or other coercion for that matter), slavery is impossible, because profit for the one providing the good or service is always a requirement. Technological advancements will not change this.
Third question: People haven't been able to more-or-less "take care of themselves" since the dawn of man. Human beings are social animals, and with rare exceptions, individuals left out in the wild usually perish quickly. We have depended upon each other since the dawn of our tribal ancestry, and with each elaboration on the technology of civilization, that interdependency increases with each stage. Unless there's something I'm missing, I don't imagine that there's some upper limit to mankind's ability to care for each other. That's all technology is, I theorize, is the propensity of human beings to specialize and fulfill some want or need of their fellow human beings. They then record this and pass it on to others and as generations pass, further specialization is built upon the last set of technological advances.
To the rest of your post, I'll speak more generally. I'm not a boomer, but I think that I have had in my lifetime some true hardship (although I understand the distinction between that and the generational kind you're referring to). I've had close friends and family succumb to early deaths due to violence, automobile accidents and disease (all before I was out of my teens, and it didn't stop there). At different points in my life I was extremely poor, to the point that I almost died due to lack of medical attention when I was a child, and I often didn't have adequately-fitting clothes, and the often second-hand ones I was lucky enough to be wearing were sometimes in rags. I had to actually go out in public and experience that humiliation. Later on in my life I had a brief bout of poverty in which I was nearly homeless. I understand that it's much worse for people in the third world, or people living through wartime, but my life has been no cake walk.
Due to that hardship, I did initially find socialist ideas attractive for obvious reasons, but they never fully grabbed me. Throughout any of my troubles, those most helpful to me were doing so voluntarily, and the coercive state did very little to help (I am hard pressed to believe that the state didn't hurt more so). I like to envision a future in which we move towards more of that, voluntary interaction between human beings. I don't have problem if the rich get richer, I just have a problem if they do it by aggression (fraud, taxation, theft, war, etc.). The income gap in and of itself should not be alarming if everyone's real income is always increasing, which I believe will happen under a completely voluntary system.
Image Attribution: HypnoArt on Pixabay https://pixabay.com/en/time-travel-black-hole-singularity-1777767/