Overall I think we just fundamentally disagree about government's role as well as for what to optimize: individual or society.

> I like this idea because I like liberty, and a rich person loses almost no agency by having some portion of their income or wealth taxed while a small stipend can make a huge difference in the choices available to a poor person.

I also like liberty, but to me the opposite of liberty is achieved when you redistribute for non public goods. Although you may have elevated the poorest, you've dampened the richests' purchasing power, however marginal. It is not pareto optimal, and to me the atomic unit is the individual and not the collective society.

> Do you have any evidentiary basis for the counter? Why would the system of voluntary charity suddenly improve its outcomes or have more money to spend?

"Crowd-out was small as a share of total New Deal spending (3%), but large as a share of church spending: our estimates suggest that church spending fell by 30% in response to the New Deal, and that government relief spending can explain virtually all of the decline in charitable church activity observed between 1933 and 1939."

https://www.nber.org/papers/w11332

This is an interesting problem due to its nature: good evidence can really only be collected once policies are in effect. Regression discontinuities around the New Deal are likely good candidates to study. The above paper estimates a 30% drop in religious charitable giving. I didn't look to see if they are able to discern whether this is due to the perception that the poor now get money from the gov so don't need extra or whether the income tax cut disposable income and thusly the charitable contribution budget.

Another instance is the Texas Seed Bill, where Grover Cleveland vetoed the disaster relief bill after finding no power enumerated to the federal government to provide aid. Private donations exceeded the Congressionally approved sum (or so I've heard but cannot find a source atm).

https://en.m.wikipedia.org/wiki/Texas_Seed_Bill

The logical basis is the following: by taxing someone you remove their purchasing power and thus naturally cut their ability to provide charitable contributions. Keep in mind the level of welfare we are already providing far exceeds what the wealthiest provide in their 50%+ tax rates. A lot of burden comes from "well to do but vunerable to economic shocks" folk, for which taxation rates have material impacts.

> If social welfare causes a significant change in the average person's risk tolerance, a claim that definitely requires substantiation, then I still might argue this isn't a net negative for the economy or society at large.

This is exactly why I mention moral hazard. We have to ask ourselves what the unintended consequences or the policies are, and how they may be abused.

Risk tolerance shifts due to free money will broadly impact the economy: you will necessarily increase demand as those with jobs suddenly find the opportunity cost of not working preferable. So you either end up with more unemployment or needing to tax at higher rates to meet the new demand for welfare. This might lead to increased economic output from the poorest but also may lead to less output from the richest. One thing is certain: risk is adjusted due to government subsidiaries/theft.

> Perhaps a person who gets the aid of charity benefits more than one who gets welfare, but does the average person?

How will you measure this? Are you quantifying strictly by the total dollars received by the needy? What if you flipped the script and asked whether the outcome is congruent to the expectations of the givers? E.g., are those dollars given charitably providing a better outcome for the givers than through dollars given by the charitable via taxation?

The benefit of the charitable approach is that there can be conditionals. "Do drugs and the money stops" kind of stuff. Society tends to think that is immoral for the government to do, but arguably the outcomes for the needy would be better if conditions were allowed. Charity also has the added benefit of being able to flow to local needs vs flow from the top down.

> If we see unprecedented unemployment due to AI, how exactly do we expect voluntary charity to expand to meet demand?

What is AI doing that will completely eridicate humans? I struggle to understand. Let's say you're displaced from programming. Could you become a farmer? Would machines undercut your price? Probably. But what if you're good at metal work and Joe is good at farming, and both of you have lost your jobs to AI? Maybe you decide to consume from only human, non AI based businesses. Suddenly, costs aside, people create an underlying economic network of non AI businesses and start to thrive again. This is essentially what we see with people trying to buy only from [insert preferences here] businesses.

I don't think AI is the scare people make it out to be. Ultimately, it will be a fun thing to play out so long as regulation is minimized.