Some of the largest challenges, honestly, simply comes down to government ID and the ability to have a mailing address for those actually wanting to be able to get back off the streets, especially if they've had theirs lost or stolen. Without these two items, they can't even get assistance like financial or medical assistance, food banks and stamps, or housing assistance. However, it's worth noting that it's not recommend to volunteer home addresses for these things for people, as there's a trust and accountability issue at play given the circumstances. It's better to get a religious house, NPO or business to provide a mailing address for them instead. This is actually one of the largest hurdles to getting help that most who need or want it face.
There's also a very largely unaddressed issue with some homeless couples, where most shelters won't take couples for safety reasons, and one of the two has significant issues that need to be addressed with the other one keeping the one out of trouble or acting as a stabilizing influence. It's hard to get off the streets when there are situations where the one-size fits most model fails. And of course, there are safety issues with some shelters as well as others have pointed out.
Most importantly, treat them with respect and expect the best out of them instead of the worst, and consider taking them at their word (trust, but verify - because some
will do song and dance sob stories and perform, though most of them do so because others who have helped them in the past set that perverse expectation for help in the first place). It's amazing how much hope someone can get from just being treated with respect and trusted instead of being treated like the dregs of society. And on that note, foster working relationships with law enforcement encouraging them to do likewise. Trust and integrity, one's word, is the only thing of true value that any one of us has... and losing everything else punctuates that reality. You can do a lot to help restore a person by treating that idea with weight and purpose with your interactions with them. It can be easy to get jaded with this sort of work, but the most effective ones are those resilient enough to not be.
It's also worth pointing out the difference between panhandlers and the genuinely homeless/squatter/car dweller types who are trying. This isn't to say that you shouldn't help the panhandlers, too, but... there's the visible homeless and the "invisible". The invisible are the ones who need the most help.
Another useful resource is a book written by one of our own from the community, though she hasn't been active or signed into her account for a few months now, so I won't bat-signal her, but I've talked privately with her in the past about some strategies in approaches for care and filling the gaps, and some of the challenges with feeding, like dental issues and chewing, general muscle strength and canned goods, cooking, etc. Anyway, book:
Rising: Strategies for the Broke, the At-Risk, and Those Who Love Them by Joon Madriga. Here's
her website, too.
Lastly, at least here in the United States and Canada, there's a very important phone number and website-related resources to remember that many of them know nothing about: 2-1-1 from most phones, or
211.org Share these resources with them, print them out, keep it handy. There's also the
INSP (International Network of Street Papers) that help a lot of homeless with re-establishing jobs that offers an alternative to panhandling.
