Matthew's version (here) are more spiritual in nature, less concrete, and therefore are easier to handle. I can deal with the poor in spirit, the meek, and those who hunger and thirst for righteousness. These are discipleship issues; a means to the end of sanctification. They preach easily.
Luke's version (here), on the other hand, are sticky and real and have been used by the powers that be to keep the impoverished and oppressed down for almost 2000 years. How can middle class Americans hear "blessed are the poor, the hungry, and those who weep" and "woe to you who are rich, full, happy, and well liked" and have them make a real impact on their lives? The poor and rich alike are lost and in need of God's grace. The hungry and full are in the same place. Even the happy and the sad are in need of God. So why is one group blessed and one woe'd?
Many of the names in my now outdated copy of Lesser Feasts and Fasts came from well-to-do families, and we celebrate their lives and ministries, but shouldn't they be cautionary tales based on Jesus' Sermon on the Plain?
I get that I'm taking this too far and probably too literally, but as preachers it is imperative that we struggle with these texts. When they make sense and are easy, we have lost their meaning. When they make us feel good, we have fallen out of God's path, I am certain. So, how do you hear blessings and woes? Do you spiritualize them like Matthew? Are they concrete? Do they bless you or curse you?