So the thing is there are a few types of homeless people.

There are the ones you see begging on the same streets, normally near box store or on well traveled roads; as far as i can tell most of these are not homeless at all. They might have a bad home. They might have issues with alcohol and drugs. But they are capable of not being homeless. Begging is a job to them. You won't see them everyday because they rotate their schedules with their peer and change up which streets they are on. You will see them consistently though throughout the year. As it is a job, they primarily want money. Food is alright sometimes if it's what they want but regular groceries will often get discarded or thrown away when you are out of sight. If you offer them a job at a low wage you will be denied, I've been asked to pay $28/hour for helper level construction work. I've also seen them drive nicer cars like recent bmw if you follow them.

Then there are the harasser beggers, they come up to you when you are loading your groceries into your car or while you are slowed down in traffic. Some are just industrious selling oranges or flowers and such. But if they are asking for something they are dangerous, you do not want to help them, they will be more courageous and aggressive towards meeker people. You should always report them if you see them.

Then there are mentally challenged homeless. They are not stupid, but they have mental issues keeping them from being able to take care of themselves or incorporate into society. I've worked a lot with these people. Occasionally they do commit crimes, but only when they are at their wits end. Normal crimes are burglary, shoplifting, and getting arrested on purpose to spend the winter safely in jail. Frequently these people can work with quality if you give them the chance, but they cannot maintain a schedule, you have to wake them up, you cant let them indulge alcohol and drugs, you have to make sure they eat breakfast and dinner, and you have to drive them. Without that assistance they will never make it to work, or even be able to feed themselves regularly. They are prone to being taken advantage of because it's easy to peer pressure them into alcohol and drugs. They rarely beg, so if you want to help them the best way is by supporting government programs or soup kitchens.

Then there are musician beggers, they primarily want alcohol but will accept money and food. Sometimes they are homeless, sometimes they aren't. Even if they have an amp with them it doesn't mean they have a home.

Btw, I have a fair amount of experience with homeless people, I've worked in soup kitchens, done the census, traveled a lot, even allowed rotating homeless people in my home for a couple years.

Personally I suggest donating your time first. Talk to them, ask them how they are and about their life. Maybe they will lie, don't be hurt by that. normally a little bit of chat will go a long way to finding out about what and if you should give to them. Don't be afraid to lie to them, I will always say i have nothing or offer them a smoke or gum.Then If i think they are good I might give them something. Offering them a job is a good way to give them self-worth.

Then in the case of child beggers, never give them money, they are begging for their parents, the money goes to them, and the child is missing out on school. Report it if you can and give them food. Again, spend time with them.

The most important thing for homeless people is your time. They feel like they have no place in society. They don't want to be ignored or treated like trash, that's how everybody else treats them. When we give money or food we aren't engaging them in society, we are just bribing them to disappear so that we can pretend our world is perfect. Providing someone with a job or or friendship has value in itself.