I've read the Sermon on the Mount many times. I've even memorized it. I suppose I never really thought about what Matthew 5:3 means, "Blessed are the poor in spirit, for theirs is the kingdom of heaven." The same verse in The Message says it this way: "You're blessed when you're at the end of your rope. With less of you there is more of God and his rule."
Now that I can understand; at least the part about being at the end of my rope. I've felt that way many many times. However I've never thought about being blessed when I felt that way.
When I looked it up in the New Living Translation it puts it this way: "God blesses those who realize their need for him, for the Kingdom of Heaven is given to them."
Either way, it shows me my need for God. When I realize I need Him then I am certainly blessed.