In a world where what happens to you in your old age is entirely determined by the choices you make when you're younger, and where the correct choices will absolutely guarantee that you have the proper resources available, this would be an excellent idea.
In my world, though, there are layoffs, long periods of unemployment, expensive catastrophic events, and generally a whole heapin' helpin' of reasons why people may need financial assistance for reasons that have nothing to do with their life choices. There are people who have done everything "right" and go into bankruptcy because a family member with insufficient health insurance gets sick. Do these things not happen in your world?
Sorry, what? Risk and uncertainty are universal. Everyone has to deal with their existence.
There have been plenty of insurance systems developed throughout time whereby people can hedge their risks. Previously however insurance was informal and consensual - you signed up to a Roman college. You and everyone else in the society engaged in it of your own free choice. If your group couldn't manage its finances it went broke (or more accurately appealed to an aristocrat.)
Nowadays we live in such enlightened times that the elements of choice and freedom have largely been removed.
The existing systems were created out of necessity, and were fundamental to the establishment of the middle class.
You talk about Roman College as if it were something available to the destitute, 70-year old serf? Come on.
Today we have millions of people working full-time jobs, making less than a living wage. That is a structural, societal problem, and no planning on an individual laborer's level is going to counter that.
How about you get back to us on your 50th birthday and tell us if the best way for minimum wage laborers to pay for basic healthcare is to beg rich people?
The only thing rich people hate more than taxes is bums. Something about moral deficiency, right?
1) Life-expectancy in Roman times was very low. 50 is a more appropriate age for your rhetoric.
2) "Serfs" are medieval. And besides, this is an argument about free citizens, so the very concept is irrelevant.
3) The colleges were all independent, spontaneously organised by poor citizens. Anyway, apart from subsidised grain and generalised patronage the Roman ruling classes didn't design social welfare systems akin to anything we would recognise (and again, the comparison is difficult, because the patricians were generally using their own fortunes to win favour with the masses)
4) The colleges insured primarily against the possibility of funeral costs in the event of sudden death - the most important shock financial event the average poor Roman expected to face. There was no effective medical technology in Roman times, but Romans cared a lot about having a good funeral and being remembered.
5) The colleges weren't "available" to anyone unless they paid their way. If you wanted that protection, you paid your membership dues. So yes, if the destitute old free citizen had been prudent and consistently paid their dues before striking bad luck, they would be okay (well, they'd get their nice funeral, but you know what I mean.)
6) Maybe your millions of people making "less than the living wage" (however you define that) should take a leaf out of the book that seems popular to users of this site - looking for ways to improve the value of the services they offer?
7) What is so wrong with the idea of people directly petitioning others for funds to purchase healthcare? Heck, they don't even need to just petition the extremely wealthy. Powerful modern technology allows people to petition the entire world for funds (if they can convince people their cause is worthy.)[1] One of the benefits of living in a more advanced age than 50BC.
8) I feel like you are imagining me wrong. To be clear: I am young, broke, and largely unaccomplished. I have no significant assets beyond my intelligence and my ambition. I have no vested interest to protect. In fact, I am someone who stands to gain the most short-term from these sorts of welfare policies. Hell, I even work for "minimum wage" currently - another thing I would like to see abolished!
I simply want society to reward and encourage people who provide genuine value, and stop forcing productive citizens to subsidise unproductive citizens, without any accountability or metrics for the benefit of their investment, because a) I want to make my way up in the world honestly, by offering true value for trade, and b) because I am concerned about the economic damage caused by pervasive, dysfunctional contemporary policy.
If society got rid of all this terrible policy, the abundance of opportunities from the ensuing economic growth would do more to improve the fortunes of the assiduous in a few years than social welfare has accomplished in decades.
In my world, though, there are layoffs, long periods of unemployment, expensive catastrophic events, and generally a whole heapin' helpin' of reasons why people may need financial assistance for reasons that have nothing to do with their life choices. There are people who have done everything "right" and go into bankruptcy because a family member with insufficient health insurance gets sick. Do these things not happen in your world?