Erich Fromm writes of various religions and their ideas as to death. He says that one emotion that
is tabooed is the sense of tragedy, and goes on to explain how various religions understood death.
Fascinatingly, he speaks of Judaism as being the only one to approach death realistically, but also
to look forward towards a time when the world would be ruled through justice- the ending days, or the days
of the Messiah.

There is a sefer published in the MeOtzar HaRav series which has R’ Soloveitchik’s profound
understanding of what it means to suffer, to mourn, and to die. He contrasts the great negation
of the individual at death with the mourning we must follow, and brings up various ideas
and connections to death. One idea I really liked was that of the Rambam’s, which explained
that the soul longs to be reunited with God, and that in those instances, death is but a “kiss”
as it is mentioned through the Torah.

The sefer is called ‘Out of the Whirlwind’- here is the link: http://www.shma.com/bookreviews/Julian.phtml
The fact that he does not negate suffering, pain, emotion, or mourning is beautiful.

My friend’s brother passed away this year, and many people did not know how to comfort her.
Therefore, they said things like, “He’s in Olam Haba now,” or “It’s better this way,” things which,
far from comforting her, only made her feel worse. I think it is a very difficult thing to
comfort mourners, and therefore the comments about Aaron were very truthful, and probably much
more meaningful because they were genuine…instead of simply a repitition of something someone
once heard about the next World.