There are some homeless in my area some of whom I’ve chatted up and gotten to know a bit. Most are middle aged/senior men who have serious medical and/or mental issues which preclude them from working.
From what they’ve told me, they tend to be wary of accepting food/drinks from random strangers unless they seen it made at a restaurant/food cart because they’ve encountered too many cases where the food/drink contained turned out to be contaminated with cigarette butts, trash, or worse because the “giver” was a cruel flaming ■■■■■■■.
A phenomenon which was confirmed by a few local cops who cited/arrested the few whom they caught in the act while patrolling the area.
Due to those experiences, it understandably took a while to build their trust enough so they would accept food/drinks from me knowing I won’t pull the same assholish stunt on them.
This also reminded me of one reason why some attorney friends prefer giving cash or buying the food/drink items in the presence of the homeless individual concerned in establishments where they know the owners/staff rather than giving them what random food/drink they happened to have on them.
They knew of cases where those who did the latter ended up getting accused of attempting to poison the homeless after the homeless individual who received the random food/drink that the giver had on him/her got sick or even died not too long after eating/drinking those items. Not worth the potential legal liability and potentially negative public reputation from all that in their view.
Regarding shelters, I don’t know about other areas…but the ones in NYC are known to have serious safety and health issues which make it understandable why many homeless may feel they’re better off remaining on the streets: