Tragedy and disappointment can both refer to the same event. If your granddaughter should end up in abject poverty due to her not finishing college, this would be the same disappointment that it is to you now, but would also be a tragedy, by anyone's description. You may have read some strange meaning into the adjective "transcendent." Your drawing of the contrast seems to imply a severe degree of tragedy. The word only refers to the fact that the tragic element transcends the mere consideration of human experience. That is, the tragedy is not so much the pain felt by the human sufferer as it is defined by transcendent considerations—like God's will not being done in one's life.Quite a range there between a transcendent tragedy and mere disappointment? I'm disappointed our granddaughter hasn't finished college but overall most pleased with her.
The analogy of God as father was indeed unthinkable for the Jewish religion...which is one reason that Jesus' teaching offended them so greatly. You might recall that the analolgy is taken directly from Jesus' teaching—especially the story of the Prodigal Son.With all the non-Christians in existence, each one a transcendent tragedy, God must be the most miserable being in existence, unless, that is, the transcendent tragedy is the future of the unbeliever. I think the analogy of God to a human father in our thinking is way overdone, something unthinkable in the ANE (ancient near east).
As for how miserable God may be, seeing those whom He loves being lost after a wasted earthly existence, I cannot say. I do think I hear grief in Jeremiah's laments and in God's mournful, "Turn, turn at my reproof, for why will you die?" (Ezek.33:11). Jesus' weeping over Jerusalem, likewise, seems to communicate this grief. What I find peculiar is that you would think this assertion strange. If you were a Calvinist, then you could argue (against the biblical evidence) that God never suffers disappointment and gladly sends the non-elect to their doom. However, you are an Arminian (last I heard), who believes that God desires all men to be saved. Are you able to hold such a view while mocking my statement that God suffers grief over the lost?