I think in the afterlife there would be no illness, money worries, traffic jams etc. It would be better up there than here but we live here and have to make the most of it. I do not think people can know everything about the afterlife for sure.
I have something to say, but do not take me too seriously as it may not be a good idea. I have read people can have a relationship with someone when they have died. You could astral project and see him. If you do this, you still have a life here. You will still need to go out with other people and have fun when you are ready. People may say, it is not fair to not let him move on. Every one has free will. He can make decisions for himself. If that is what he wants then he would let you know. As I said, do not take me too seriously as I do not know if it is a good idea.