More people SHOULD bequeath money to the homeless, but the real question is if they will, no pun intended. More people SHOULD volunteer to help the needy, but it doesn't mean they are going to spend their valuable free time on others. I was once homeless and a little help would have gone a long way then.
In theory, this is a great idea. If you can afford to leave money to the homeless or to charities in your will then I think it's a great idea. I think a person should choose how they give away their money in their will. If they want to take care of their family, I think that's fine to.
The number of people who win the lottery and end up broker than when they started kind of speaks to how little bequeathing money to the homeless would do.
Realistically, we need to ask why each person is homeless, and try to fix the root causes. As well, should anybody really be obligated to do anything for anyone else? The obligation takes away from the charitable spirit, and ends up with more people doing less.
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If someone wants to leave a homeless person money in their will, let them. If someone doesn't want to leave a homeless person money in their will, let them. But should we be waiting for people to die to help the homeless? How about we help the homeless and less fortunate during the time we're alive on this Earth?
A better way to help the homeless than a direct bequeathment, is to will money to a charity that helps homeless people. By giving to a charity, you can be sure that the money will not be used for drugs or alcohol, or that you are not being tricked by a scammer. For money to really help, it needs to be directed to a charity that can not only help feed and lodge the homeless, but also help them put their lives back together through effective social work and medical treatment if necessary.