That’s what I summarised, aside from the us-centric references. I still don’t quite understand the emphasis on “true individual liberty”, what that should entail and the meaning of it for the discussion. I agree with everything else you said, that part just isn’t clear to me.

What’s your definition of liberty here? Just the absence of constraints? As in to be free from sth., opposed to being free to do sth.?

If it is, then sure you can have individual liberty. It’s just (almost) utterly useless. Or do I not get your point here?

It’s important to think about the counterargument, I agree.

To counter your counterargument: it’s not a good argument on many levels (scope, allocation, distribution mechanism, effect). The main reason is that this sort of charity doesn’t improve the core problem of low(er) social mobility. The opportunity to pursue self-development/self-fulfillment should not be tied to the whimsical act of a better-off person but presented to everyone as equal as possible - through common goods and services. The impossible future is impossible due to vastly different prerequisites. The person’s “greatness” will never be seen, as most likely they will never be presented with the opportunity to display it.