The Startled Poor

How startling would it have been to be poor and hear Jesus say, "Blessed are you"? What if you were mourning? Something that brings such hardship and is seen as a curse in some (most) cultures is now being told to you is really a blessing. It is really an interesting question because I have never really read that blessing from the standpoint of the poor or the mourning, or for that matter, from the standpoint of the humble or meek. I have generally always read it from the standpoint of the comparatively rich and the non-mourning. I typically read the blessings from the standpoint of the selfish and prideful. Of course I typically read those beatitudes and blessings and speak of "God's upside down kingdom" and the direct challenge for me to realize the life changes it would mean for me. So I stay rich, selfish, and prideful because those changes seem so hard to make. But what of the poor hearing that they are blessed? What of the humble, meek, and mourning? Would it be freeing? Would it be confusing as it doesn't FEEL like a blessing? How would that have felt to be told that? I honestly cannot imagine because I am rarely ever an of those things.