First we have set aside the more familiar 'beatitudes' found in Matthew's gospel. 'Blessed are the poor in spirit'. Matthew gives us a spiritualised, set of attitudes. To discover the more material, gritty slant of Luke we need to work out what sort of congregation he has in mind.
By the time the Gospels were written, the new congregations that had sprung up were city dwellers. Luke was clearly an educated man. This implies that his family were of some standing because education was expensive. Whereabouts did Luke write? In a city outside the Holy Land certainly. Antioch is one suggestion - possible but not provable. What were his church members like?
The lives of peasants in Galilee where Jesus centred much of his ministry were precarious. They were peasants dependent on what bare subsistence they could wring from a plot of land, not of the best - the local rich controlled the best arable land. The average peasant was crushed by the rent he had to pay on his plot and by excessive taxes of various kinds. He was at the mercy of locusts, famine and every misfortune possible. He died young - forty if he was lucky. His wife was exposed to the hazards of childbirth. Widows and orphans were common.
But urban life was no soft option - there was a vast gap in wealth between a very small minority and the average city dweller whose existence was fully as precarious as a peasant's. Writing to the Corinthians, Paul says 'Consider, brothers, how you were called; not many of you are wise by human standards, not many influential, not many from noble families' (1 Cor 1.26). The implication is that a few disciples were well off and distinguished.
Suppose that Luke's city congregation had a few well-placed members (including Luke!) but were mainly poor. Most of Luke's congregation were dependent on finding such work as was available on a day to day basis - their situation was akin to the labourers in the vineyard. If unlucky on a particular day, there might be no food on the table. Those too crippled, worn out or handicapped even to seek such work would be forced to beg. These would be not just poor but destitute. There were many who were homeless. Their health no better than a peasant's, their lifespan equally short.
What of the few members of the congregation who were better-off? Their support of the life of the congregation would be very necessary - and also difficult far beyond any financial aspects. By joining the despised and disreputable Christians they would be stigmatised and shunned by their well-off friends and lose whatever power they had formerly enjoyed. There would be no more exchanges of banquets and the like social events. Luke himself would surely have experience of such deprivations.
Luke's Beatitudes are addressed to two sections of his church. Many were destitute, hungry, mourning and despised by the local population. At the economic level they are certainly not blessed. Yet Luke calls them blessed!
But of the rich (potentially ex-rich?!), Luke's Gospel is very demanding. They could foresee a future of being in very changed circumstances. What they lost by their discipleship would be doubly hard to bear. Being a disciple and living up to Jesus's exacting demands could beggar them. Was this too much for some of them to face? The Gospel directs the four woes at them. Rich, well-fed, laughing you rich may well be now but what would you be if you heeded the call to discipleship? You might take the beatitudes to yourselves then and also be paradoxically be as blessed as the poor!
The prophet Habakkuk lived in very difficult times; all sections of Luke's hearers might to see themselves as blessed - however paradoxically - and take to themselves what Habakkuk realised:
For even though the fig does not blossom,
nor fruit grow on the vine,
even though the olive crop fail,
and fields produce no harvest,
even though flocks vanish from the folds
and stalls stand empty of cattle.
Yet I will rejoice in the Lord
and exult in God my saviour.
The Lord my God is my strength.
He makes me leap like the deer,
he guides me to the high places.