I'm thinking of making my son homeless for a couple of weeks
Why would you want to harm your own son by making him homeless?
He is too privileged so I want him too see what it's like to have nothing.
I understand that you want your son to learn the ways of how other people live, but making him homeless is dangerous. Take him out into the community and let him help people to get to know their plight instead.
I think it's good that he will be able to learn real value of life by becoming a homeless, it will definitely be a better experience than just hearing about it.
There are other ways to show your child how others live. Have you thought about having him help out at a homeless shelter?