moish, your definition of the word fair sort of answers your question. Every person gets what he needs (we’ll skip deserves for now) to be the best person he can be. God doesn’t compare you to your neighbor, He compares you to the person He knows you can be.
There’s a famous moshol (don’t know where it’s from) about a man who trained his whole life for mountain climbing. When he made his longest, hardest trek up one of the world’s tallest mountains, to his great disappointment, he saw a young boy up there. The man was devestated! He worked so hard for so many years to get here and this youngster, in his short lifetime, was up here already! What the man did not know, was that the boy was born at the top of the mountain.
moish, in your example, the first guy was born on top of the mountain, no sweat. The second guy, it was hard for him, he worked for it and got there.
Hashem doesn’t necessarily look to see where you are, He looks to see where you came from and what kind of effort you made to be where you are. People might appear to be towards the lower half of the mountain, but they could very possibly be far, far ahead of someone who seems to be at the top.
~a~