In my opinion, the best approach is to be as involved as possible in the process. Get as close as you can to direct giving, rather than blindly trusting in organizations (which are often unfortunately corrupt). If you can get involved with an organization, then you can see it from the inside, which is the best method of vetting out there. Or you can do your own thing. It is also good to research what is truly needed in order to help people escape their situation.
For example, in order to be able to get a job, people will typically need:
1. A permanent address of some sort that they can use on their resumes and any employment paperwork, or else they will have to lie about it and may be caught and fired.
2. Reliable transportation, even if it's just a bus pass. But they need something reliable.
3. A phone, in order to be able to be reachable by interested employers, set up interviews, use the clock to keep time, etc.
4. A way to keep the phone reliably charged.
5. I.D. (state or driver's license in the states)
6. Their social security card or a copy
7. Access to bathing and laundry (they likely won't be hired if they have dirty clothing or smell bad)
8. Interview-appropriate clothing
9. Internet Access (not all libraries are free to use, some libraries also require I.D., etc etc) How are they going to search and apply for jobs without the internet hello
And so on. All of this is necessary just to get a part time gig at Walmart, let alone a job that is actually sustaining.
So if you want to make a difference, you have to buckle in and get strategic. Research the needs. Think about what you would do to get a job if you were suddenly homeless with nothing but the clothes on your back. If you're thinking critically about it, you will quickly come up with all sorts of obstacles and issues that would be in your way. Those are the ticket items.
In fundraising ads, explain specifically what is needed, why it is needed, and how providing this need will help people get back on their feet or remain on their feet. This gives people confidence when donating, rather than a situation where a group/organization/shelter/church/etc is like.. "Please give us the money, and we will make sure it goes to a good cause." Most people do not trust that. If most people are more inclined towards greed, and something seems sketch, then it's like, fuggedaboutit. But if you can point them to something specific, explain specifically why it is needed, specifically how their donation will provide that need, etc, and are very transparent about the process, then that is more encouraging.
Some needs are already met, and a community's homeless network know all about it. Getting enough to eat, for example, is often pretty doable, because so many charity events and shelters focus on food. So a fundraiser for food might not get much traction. But what is often overlooked is that most homeless people must walk 15-25 miles a DAY to get to the places where they can get food, or a bed, and so on, so they are rapidly burning off the calories they are getting, plus their feet are in bad shape, etc. Thus bus passes are a HUGE deal. And so on.
I'm all about charity, but I want it to be strategic.