I agree here, this pilot may have died of cancer or was hit by a car in '55? Fun Fact - Some of the Air force(British/American/Japanese/German etc.) actually made it out of WW2 alive!
And who's to say that reincarnation means you move straight into your next body/form anyway? If you believe in reincarnation surely you can beleive in going into a state of purgatory/heaven aswell? We don't know what Jobs beliefs were, even if he followed a religion, everyone has their own version of their religion.