Why do bad things happen to good people ? I think Rabbi Simmons perspective captures it
(Taken from here
Why Bad Things Happen to Good People - Judaism )
GROUND RULE #3 - ETERNITY
The question of "why do bad things happen to good people" has a lot to do with how we look at existence. The way we usually perceive things is like this: A "good life" means that I make a comfortable living, I enjoy good health, and then I die peacefully at age 80. That's a good life. Anything else is "bad."
In a limited sense, that's true. But if we have a soul and there is such a thing as eternity, then that changes the picture entirely. Eighty years in the face of eternity is not such a big deal.
From Judaism's perspective, our eternal soul is as real as our thumb. This is the world of doing, and the "world to come" is where we experience the eternal reality of whatever we've become. Do you think after being responsible for the torture and deaths of millions of people, that Hitler could really "end it all" by just swallowing some poison? No. Ultimate justice is found in another dimension.
But the concept goes much deeper. From an eternal view, if the ultimate pleasure we're going after is transcendence - the eternal relationship with the Almighty Himself, then who would be luckier: Someone who lives an easy life with little connection to God, or someone who is born handicapped, and despite the challenges, develops a connection with God. Who would be "luckier" in terms of eternal existence? All I'm trying to point out is that the rules of life start to look different from the point of view of eternity, as opposed to just the 70 or 80 years we have on earth.