I think a lot of what you say here is about unhappy people. The day my grandfather died he said he was proud of what he had done with his life, and he was ready to go. He was never a religious person, and he didn´t believe in god. He had a long life, he used it well, and he was done. Some people are happy with this, they don´t need to have more. He had raised his children well, all his grandchildren had also become adults with good jobs and happy lifes, and he even had wonderfull times with his great grandchildren. Perhaps it´s hard for some to believe, but he didn´t need the notion of heaven to be okay with the idea of death.
I don´t think "betting on God" is a win-win situation. Sometimes people use the idea of heaven to not do anything about making the world better today. They limit their good deeds to not creating a better world, but to getting "plus-points" on the scoreboard to heaven. Parying five times a day at home for plus-points, instead of going out in the real world and helping people... That is why I don´t count on the idea of heaven. If I would do that, I would accept all miserable things in life and not try to make them better. I would see life as a waiting room, instead of the wonder that it really is. I don´t want to live my life like that. I believe, if you get the best out of your life itself, you don´t need to believe in afterlife to be happy.
I dont want to talk after a dead person so I will not make a comment about your grandfather.