I read some commentary the other day by someone who thought that Jesus’ Sermon on The Mount sounded like a lot of nonsense. I replied that to think the beatitudes are nonsense is actually a GOOD sign, in that you are hearing in them exactly the shocking impossibility Jesus INTENDED people to hear. Long familiarity with them causes many Christians to simply hear a singsong of vaguely inspirational words. As I’ve said elsewhere, one of Jesus’ primary rhetorical techniques is one of hyperbole.
What he presents here (and many of the beatitudes go back to some of the earliest Jesus material – Q1) is supposed to be a shocking declaration that the real winners in life are the poor, the meek, the sorrowing and the persecuted. It was to these people that Jesus sees his primary mission (“The Spirit of the Lord is upon me, because he hath anointed me to preach the gospel to the poor; he hath sent me to heal the brokenhearted, to preach deliverance to the captives, and recovering of sight to the blind, to set at liberty them that are bruised”)
The key to understanding them, in my opinion, is in the first verse. “Blessed are the poor in spirit: for theirs is the KINGDOM OF HEAVEN” (Or as it is reconstructed in Q1 – “How fortunate are the poor; they have God’s kingdom.” ) The rest of the beatitudes are to be understood in terms of the “Kingdom of God” – a state in which everything will be reversed, the first will be last, the proud will be humbled, the humble exalted, the mourners will rejoice, etc.
The only question is, just what IS God’s kingdom. Opinions vary.
Some believe it primarily represents a future state in heaven.
Some believed it represents an earthly social reality Jesus wishes to establish.
Some (I would fall into this camp) believe it primarily represents an inner spiritual reality.
Many of those who primarily fall into one or the other camp also believe the other two are, in some sense, also included.
But in any case, it clearly doesn’t represent the state of things in the common, day-to-day, unsanctified world, and hence your observations that it seems nonsensical compared to everyday reality.