Dude. “Progressives” is a big span of people and ideas. “Give more shit away for free” is not a policy position and you know it. Do I like things like land grants (an actual progressive policy idea)? No, personally I’m skeptical. What we do need to be looking at though is things like the cost of health care, the cost of child care, access to education (including cost of student loans) that push people into economic hardship and ultimately into homelessness. Likewise - regardless of politics - we all recognize that we are in an enormous mental health crisis as a nation. You work on these root causes and work your way back into solving homelessness. None of that involved “giving away shit for free” and none of it happens overnight.
That said - maybe you should look at places like Houston, which is hardly a liberal hotbed but I understand has improved their homeless problem by… giving away free housing.