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I would say the answer to this question is probably best answered on a case by case basis.

How you might be able to discern each case, I'm not sure, without having some kind of practical experience or knowledge, or some type of observation, but one answer does not fit every situation is where I'm going with this.

The term poor will mean different levels of it depending on where you live, too. In the case of the U.S., homeless folks are generally among the poorest, but they also can have a host of different issues, which can include (but not always—thus the discernment), alcoholic or drug related addictions, which may or may not be because of PTSD or some kind of continuing trauma, either psychological or physical.

Poverty can come from many different circumstances, including ones that are somewhat self-induced for one reason or another. In those cases, handing someone some money isn't going to solve the problem, but help to keep it going. What needs to happen is an unraveling of decisions and behaviors that have spiraled them into the current situation.

However, there are plenty of times where $10 is what a person needs to get by. It's probably going to be more than that, and more than one time, but it's not treatment or something like that they require, but more of an opportunity. In that case, money might not be the answer either, but a chance to work.

Depending on the country one lives in, there could be all kinds of resources for the poor, which would include some kind of benefits, as well as employment training and opportunities. These can be governmental or provided through non-profit or charitable organizations such as a church.

Those who are Christian have been commanded to 'help thy neighbor', which might mean a one time gift of money, but it could also mean a lifetime of friendship, which could include hours of service, along with sharing of resources. But nowhere does the Lord ask that we be taken advantage of, or that we put our own situation or family in a precarious position. So, all of this must be done with moderation and within the time and needs we have.

That is a verry detailed answer, and I could'nt agree more. It all depends on the peson, sometimes it's good to give, sometimes it just encourages more problems.