Before I take up the wonderful insights you offer, I want to place the second beatitude in its Jewish context. In a sense, there is nothing new in Jesus’ teaching. The first two beatitudes repeat the classic messianic mission set forth by the Prophet Isaiah, the mantle of which Jesus may be taking upon himself.
Isaiah tells us that “because HaShem has anointed me [that to say because God has made Isaiah a messiah, an anointed one], God has sent me to bring good news to the humbled, to bind up the broken-hearted, to proclaim liberty to the captives, and release from bondage to those who are bound,… to comfort all who mourn,” (Isaiah 61:1-3).
Images of God comforting mourners is fairly common. We them, for example, in Isaiah 40:1; 57: 18; and 60:20. Then there is the notion that suffering, and the mourning it invites, is part of the redemptive process. Psalm 125:5 says, “They who sow in tears shall reap in joy.” And Psalm 94:12-13 says, “Happy is he whom You chasten, HaShem… that You may give him rest from the days of adversity.”
In other words, Torah makes it clear that suffering is often a gift from God, and that those who mourn are to be comforted. Again the Prophet Isaiah tells us that “sorrow and sighing shall fly away,” (Isaiah 51:2), and that God will comfort the people (Isaiah 66:13).
My point is simply this: Jesus is drawing upon well-known and well-accepted doctrine in this beatitude, and I don’t see where he “turns normal expectations upside down,” as you put it. On the contrary, Jesus isn’t saying anything new, but rather laying claim to something very old. He is identifying himself with the messiah idea of Isaiah. His Jewish listeners may be startled that he is claiming the messianic mantle, but there is nothing about that mantle that is knew to them.
But, because you assume that Jesus is teaching something new, you raise some very interesting points that my more Jewish reading might have missed. So let me comment on your teaching.
Jesus is calling us to a new life, and following him requires the death of the old life. I believe this is what all great wisdom teachers teach. The egoic life is a block to the greater life of the soul, that level of consciousness that knows all life to be a part of the One Life that is God. We have to let the old life die, and do so respectfully, which means with authentic mourning.
If our mourning is not true, our transformation is false as well, and no real joy or comfort will arise from it. And because this new life is not ego-centric but world-centric the pain of the world becomes our pain. We become compassionate, literally sharing (com) the suffering (passion) of the world. The Passion of Christ is paradigmatic of the passion through which each of us is to pass as we move from ego-centric to world-centric to God-centric consciousness.
I think what you are saying is that when we become part of the Greatest of These (God) we cannot help feel for and act on behalf of the “least of these,” to borrow from Matthew 25:40.
I especially like your closing idea that both takes us back to Isaiah and puts forth the way of the Kingdom of Heaven. When we fully participate in the Life of God, that is when we realize that we are manifestations of God, the way God is alive in our time and place, we take on the work of God: “to bring good news to the humbled, to bind up the broken-hearted, to proclaim liberty to the captives, and release from bondage to those who are bound,… to comfort all who mourn,” (Isaiah 61:1-3).
What began as the work of the Messiah becomes the work of each one of us. While faith may be the way to the Kingdom of God, action (deeds) is the way of that Kingdom.