Well, and its worth noting that people did make the choice to not live in generational households before, and not everyone had children, and not everyone was outlived by their children, thus the old people living in poverty in the first place at the founding of social security. Having the freedom to go off on your own is definitely a great thing. But if you choose not to, you can't take advantage of numerous tax advantages and breaks that come from incurring certain expenses. In essence, if you don't live the life envisioned by the nanny state, you are paying extra taxes to subsidize those who do.
As for social security being a work in progress, well, it's been quite a long time since life expectancy significantly outstripped viable working life, and we've made zero improvements to social security (and there's solid arguments it has gotten worse) and also zero progress on financial literacy. As someone who had to take a standardized test every single year in school starting at grade 2, but was never once required to take a personal finance or home economics class, I'm just glad I encountered enough people who cared about me to start me on the path to FI before I was too far in debt to be saved.
I also don't see steps towards integrating seniors into the workplace more. Most of the seniors I know who retired would be fine to keep working, they just can't do full days/5 days per week. Fuck that, most people I know period would rather not have to work 5+days/wk, myself included. I'd happily take a 60% pay cut and work only two days a week, if I could find that job. But if you really want to go down a government regulation rabbit hole, "standard work week" and all of its ramifications is a great place to start.
The complexity of the world we live in is such that virtually any failure you want to point to in society and blame on a company or on people, government isn't some powerless thing standing by that would help if only you vote for the right politician, rather it is a complicit and active participant, if not initially, then certainly now. The thing that was started to keep people from having to do more than that becomes a thing that requires them to do at least that. And so you find out pretty quickly if you try any nontraditional business model that swimming against the grain is heavily discouraged. You are "avoiding your obligations" by hiring only part time workers, etc.
Re: UBI. Like I said, I like UBI, but where it fails to be a scalpel is that the level of tax required to support any meaningful UBI would itself be a fairly large hurdle to overcome. As a blanket applied to everyone it is definitionally not scalpel-esque (of or pertaining to scalpels, let's spell scalpel one more time!). So UBI gives the person making $2billion/yr the same as one making $0/yr. That's equal but it isn't what the person making 2bil needs or wants. She'd prolly prefer the right to park anywhere or a couple free murders in this lifetime. What you're talking about is after we've decided to have a social safety net, and I 100% agree that UBI is the best way to have that safety net. But the tax burden of maintaining the social safety net will be high, and arguably it will be high regardless of how productive we as a society become. Maybe that's OK, maybe it's the best way, but taxes are to the free man what burdens are to the slave, no shame in shirking them.