Lots of people wake up and never evaluate their life at all. People win the lottery and end up homeless with a drug addiction. If millions of dollars can't help them, do you think the government should keep writing those people checks?

This is a strawman argument, because this is in no way representative of the many people who live in poverty, but I’ll address it because it doesn’t change my final opinion:

Yes, because obviously what someone who won (and lost) millions of dollars needs is not money, but help and support.

Not to mention, by the construction of your own strawman, if they’ve won such a jackpot they’ve probably also then paid millions in taxes.

I don't see how this is a strawman. My argument is an existence proof. There exists people who cannot be lifted out of poverty by giving them money. I can trivially prove my claim by giving examples of such people[1]. I never claimed that all or most people are like this. But its undeniable that some people are simply irresponsible / lazy.

[1] https://www.thestar.com/news/gta/2016/08/15/5-million-lotto-...

"Some people" is not "all people" and certainly not "almost all" people or even "most people".

I'm curious to know your position on those who are homeless -- as if mental illness, systemic neglect, and abuse combined with skyrocketing housing costs such that even otherwise-able people are just a few missed paychecks away from foreclosure) are incidental, and it's really a result of being "lazy".

I don't have any personal experiences with homeless people, but my understanding is that the vast majority of the homeless suffer from serious mental illness / addiction. I think that's a categorically different thing than those unwilling to improve themselves (which I do have personal experience with).

Being homeless would rob nearly every opportunity from you. I don't think it would be fair to dismiss those people as lazy, if all the hard work in the world wouldn't do them any good.