Became friends with a number of homeless, bought them meals, gave them money, gave them clothing, heard their life stories in their own words, etc. There used to be a lot near where I used to live.
How did you meet? On the street? At a shelter? Most homeless people are homeless under a year in the US. Many have jobs. Many sleep on couches not streets. Or in cars not shelters. And they try to avoid the stigma of homelessness.
Agencies and researchers talk about 2 or 3 kinds of homelessness. Longer than 1 year is chronic.[1] 120,323 of 580,466 homeless people counted were chronically homeless in January 2020.[2]
I don't think the number with jobs is tracked nationally. 10% of unsheltered people in San Diego said they were currently employed or attending school.[3] Another 11% were unemployed under 6 months. In New York City 16% of single adults in shelters had jobs.[4] 28% of families had at least 1 working adult. And people with jobs spend less time in shelters or on the street of course. Maybe none if they can afford a cheap hotel room.
You meet who you meet on the street because people with somewhere else to be are somewhere else.