The key word from the Greek text for today's Gospel passage in the liturgy (Luke 6:20-26) is "Μακάριοι" – "Blessed". In the time of the ancient Greeks the word was a reference to gods. It also was used for those who had died as they were considered "blessed" because they were now inhabitants of the other world where gods lived. Later "Μακάριοι" denoted the elite in society – the cream of the crop, the wealthy and powerful. In Old Testament usage "Μακάριοι" pointed more at men who lived righteously and were rewarded with wisdom, an abundant harvest, and a good wife who brought forth many healthy children.
Taking all these definitions and throwing them into one pot while also adding to it the Authority of Jesus Who speaks these Beatitudes, you get a sense of the magnitude of His words, plus the holiness He attaches to "Μακάριοι" and the seriousness of our calling as Christians.
To the unbeliever this would have to be considered a ridiculous Gospel passage. How could anyone be called blessed who is poor, hungry, weeping, hated, excluded or insulted?
A healthy prayer life, frequent Confession and the Eucharist rewards us in this life with some heavenly wisdom. Worldly wisdom would portray these conditions as horrid; and from that perspective, who could argue that? Ever notice that divine proclamations and human logic are usually exact opposites?
Setting aside the literal meaning of "poor," the first Beatitude calls us to be beggars before God, trusting in His Providential care.
To be "hungry" in a middle to upper class existence is to be actively involved in flooding the culture with moral righteousness. It is an unquenchable desire to see a change in the secular attitudes of society.
The devout are "weeping" because of the evil which not only tempts lives but sadly also conquers some. This is coupled with a longing for the peace and goodness of the heavenly Kingdom where evil has no abode.
Remaining steadfast in faith could very well make us victims of insults and hatred, but courage in such cases promises a great reward in heaven.
Some English translations opt for the word "happy" instead of "blessed". That really is not a good translation of "Μακάριοι". Saint Jerome, who knew the Greek language, confirms this when he translated the Sacred Scriptures into Latin and chose the word "Beati" (Blessed). Understanding "blessed" as the proper rendering should heighten moral convictions and deepen our own desire for a more loving communion with Jesus which was made very attainable by His Incarnation; for the opposite of happy is merely unhappy but the opposite of blessed is cursed.
"Woe" is an interpretation of the Greek word "Οὐαὶ" which is not an exact definition but probably the best word that English can offer. "Οὐαὶ" is an expression of grief; or in a stronger, harsher sense reflects damnation.