> It seems logical and reasonable to give more help to those who need it more.
It does, but that is because all the counter-arguments are complicated and sound mean-spirited. That approach, when tested, sometimes works out absolutely terribly.
Liberty and assuming everyone has an equal capacity to better themselves is the winning philosophy.
Helping people who need it is a lousy strategy. Giving them opportunities is a great strategy. However, the opportunity needs to be to show that they will work hard for a goal, not shoehorning them in to university. Nobody needs a degree to succeed. They need safe shelter, clear/consistent/unbiased rules, food and a system that allows accumulation of capital. A good universal level of high school education. The basic foundational things that underpin a civilised society.
> And realistically, you're always going to be way better off by maximizing your own success
Most people don't actually work that way, I don't have a statistic but based on anecdote I'd expect most people to minimise risk. People who optimise for success are quite rare.