Tough question. Here in Md. we have had an influx of people called zingari, sometimes romani and if they are Irish, travelers. These people will accept alms with one hand and steal from you with the other. They amass more wealth than working folk. You want to stay away and let the police handle these.
Sometimes I’ll see people of every race, creed and ethnicity on the road begging. As I approach I either smell the alcohol from six feet away or their crack pipe didn’t make it all the way into their pocket. These people are more at risk because when they are homeless and it freezes like it is now, many homeless shelters will refuse to admit people who can’t pass the pee test for drugs and alcohol. But if you give them money, it will go to drugs and booze. I usually give them food. Sometimes the army surplus store will have fantastic sales on outerwear, thermal blankets, hats and gloves. I’ll buy what I can and give them out as needed.
The hard ones to identify get up, leave the shelter, take their kids to daycare, work their job as if they don’t go back to a shelter that night. This problem’s above my pay grade.
Another difficult group to find is elderly people in private homes and independent living apartments who don’t have enough food to last through the month. The solution is more complex because the person may need something as simple at a ride to the store, help with budgeting or some have needed some cooking done for them.
Figuring out how to help is an art and you should expect some trial and error. Everybody has an opinion on the subject. I have found that the people who do the least for the poor are the loudest when criticizing your efforts. With trial and error you’ll filter their noise out.