This (paywalled) Yglesias piece really gets to the heart of the "homelessness issue". When you hear folks complain about homelessness, that's not what they're actually complaining about.
America’s two homelessness problems
Homelessness appears to be on the rise on American cities, though by amounts that are much more quantitatively modest than most casual observers seem to think. And to an extent the disjuncture there reflects the fact that the homelessness problem is arguably two different things. Or at a minimum, the homelessness problem that the Department of Housing and Urban Development counts and the homelessness problem that normal middle class city residents complain about are two pretty distinct phenomena.
slowboring.com