There are some good answers in the posts above. Here are some more ideas:
A used laptop or pad is a great idea. Pawn shops have the best prices.
I would research how, in this guy’s immediate area, one registers for an EBT card (food stamps). He is definitely qualified, but he needs an address other than a P.O. Box for them to send it to him, which presents a second problem. There are places that provide the homeless addresses such as certain churches and homeless shelters. I would contact the church nearest his on ramp to see if he could use their address. A nice lady lady will get better results with the church people than he will.
In order to get an EBT, he also needs an official picture ID, such as a driver’s license, or a state ID. Many states offer State Identification Cards for a fee since 911. I would find out how much the ID is, what he has to do and where to go to get one. But, he is going to need a certified copy of his birth certificate and a Social Security card in order to get one of these. That’s a whole new bag of worms.
No matter what you do, or how involved you wish to get into this, this man can always use transportation to and from better prospects. You could buy him a monthly or annual bus pass. If he has any paperwork showing he is homeless, he might be able to get an annual bus pass from his city or county. In my former county in Florida, they just instituted a program that if someone possesses a county indigent health program card, they automatically get an annual free bus pass, a hard plastic card with their photo embedded, which solves a lot of ID problems as well. You might look into whether or not your county or city offers something similar.
IDs and transportation are huge problems for the chronic homeless and keeps them from many of the indigent programs offered by local and federal government. If you could help this guy solve just one of these problems, it would be more helpful than anything else you could do for him. An EBT card will him about $100 worth of cold, prepared food, ramen and canned goods every month. It helps.
Many shelters and churches won’t touch this aspect of the homeless. It’s too involved, it often takes too many resources. It is much easier to feed and bed the homeless than it is to connect them back into the world.
The reason is that a large part of this population suffers moderate to severe mental illness which goes undiagnosed and untreated resulting in their homelessness. The characteristics of these illnesses aren’t conducive to things requiring the ability to be proactive, to plan ahead, or to make any decisions based on anything other than exigency.
Then there is the problem that, even after they accrue all the things they need to get the IDs to enroll into indigent programs, all their shit is stolen and their IDs with it. Or they lose their stuff, or the cops just take it away while they are at the 7–11, or they are arrested and taken away for a few days and their stuff is missing when they return. And it’s back to square one.
It’s a real shitty life and you just give up after awhile and coast as much as you can until you die. It is no surprise to me that indulgence in a little anesthesia along the way is so common among this population.
You can also find out how to get the guy a free government cell-phone by googling “Obama phone”. These are usually basic phones with free 250 minutes calling time per month with no roll-overs. This can be an invaluable device. If he is willing to give you his info and a safe address it can be mailed to, you can arrange the phone for him on the net.
I don’t know how much time you have on your hands, @Jeruba, but you seem to keep revisiting this theme over the years, so I assume you are interested in real solutions. You might look into what your county has available as to getting these people IDs and transportation and see if anyone is actually speciallizing in this aspect of the chronically homeless.
Don’t think for a minute social services are on this. They don’t provide safe mailing addresses, they don’t help each individual navigate the various obstacles each state has between them and a birth certificate, they don’t leave their desks, rarely look beyond their own county or state for resources and almost never connect with private orgs outside of their immediate geographic area.
There are programs galore for these people, but nobody will take the time to properly connect them because helping someone who really can’t help themselves—due to mental illness, substance abuse, or just failure to thrive— is very, very difficult.
You might look into starting an org that fills in this gap. I might be something you can do in, oh forty years from now ;.), when you retire. A kind of one-stop clearing house specializing in getting ID’s and registering people into programs and transportation and disseminating useful information, like free tuition for the homeless at your colleges. Many of these programs are big secrets for some reason. They pop up and disappear regularly. Constant research is necessary to stay on top of these, but computers and the net are wonderful things. You might have some like-minded friends who would also like to get involved. You might create a model that could be replicated throughout the country. Ransack your book or writer’s club for help. They always seem like nice intelligent people.
Sorry about the length. It’s a complicated problem.