The Sermon on the Mount: Section 42, A--Blessed are the poor in spirit.

Section 42
 THE SERMON ON THE MOUNT
 (Concerning the Privileges and Requirements of the Messianic Reign. A Mountain Plateau not far from Capernaum.) 

Subdivision A
INTRODUCTORY STATEMENTS
MATT. 5:1, 2
LUKE 6:17-20

The Fourfold Gospel gives this framework:
"While spoken to all, the sermon was addressed to the disciples, revealing to them the nature of the kingdom, and contrasting with it: 1. Popular expectation; 2. The Mosaic system; 3. Pharisaic hypocrisy."

"According to Matthew, these beatitudes are nine in number and seven in character, for the last two, which concern persecution, do not relate to traits of character, but to certain external circumstances which lead to blessings." -FG

From Pulpit Commentary:
THE SERMON ON THE MOUNT
The following may serve as a brief summary.
1. The ideal character of his disciples (Mat_5:3-10), which must be allowed to appear (Mat_5:11-16).
2. The relation that they ought to hold towards the religion of the day, of which the Law was the accepted standard (Mt 5:17—6:18).
(1) The fundamental principle of this relation is found in the relation which Christ himself holds towards the Law (Mat_5:17-20).
(2) Their relation further defined by illustrations taken from the religion of the day, as this is seen in—
(a) Cases deduced directly from the Law (Mat_5:21-48).
(b) Cases not so deduced (Mat_6:1-18).
3. General principles regarding—
(1) Their relation to wealth. They must remember that only the single eye receives the light (Mat_6:19-31).
(2) Their relation to men. They must remember the dangers of differentiating others. They must treat them as they would themselves be treated (Mat_7:1-12).
4. Epilogue (Mat_7:13-27). A call to decision and independence of walk (Mat_7:13-23). Assent is useless if it becomes not action (Mat_7:24-27).

Subdivision B
BEATITUDES: PROMISES TO MESSIAH'S SUBJECTS
MATT. 5:3-12
LUKE 6:20-26

For many years, I've favored the book of Romans as my "favorite"-- give me nuts and bolts all day long, lay out the grand scope of the inter-workings of God's plan for humanity.  But, I've grown to love the quietly powerful Beatitudes--perhaps equally--over the last stretch of years.  They succinctly address the deepest needs and questions of our heart.  They point to an unexpected path.  Compact, piercing, universally applicable, and straight out of the Lord's mouth, they are a tour de force that makes no sense outside of the Father's Kingdom.

"And he opened his mouth. Frequent in the Old Testament; e.g. Job_3:1. A Hebraism, indicating that the words spoken are not the utterance of chance, but of set will and purpose." -Pulpit Commentary

F.B. Meyer:
There are many doors into the life of blessedness. It does not depend on outward possessions, such as worldly goods or high birth. There is no soul of man, however illiterate, lonely, or poor, that may not step suddenly into this life of beatitude and begin to drink of the river that makes glad the city of God. Our Lord lived this life before He described it. He has opened the doors for us. If you cannot enter by the gate of purity, can you not come in by that which is reserved for those who hunger and thirst?

On the word "blessed"---Vincent's Word Studies has a lovely meditation and analysis of the word "blessed" in Matthew 5. He contrasts the Greek conception of blessedness (essentially earthly, having to do with money, power, and intelligence) with the Christian conception (an inner state, characterized by faith and love, definitely moral).  The Greek conception is confined to the earth, while the Christian conception points to Heaven.

Blessed (μακάριοι); Vulgate, beati; hence "Beatitudes." The word describes "the poor in spirit," etc., not as recipients of blessing (εὐλογημένοι) from God, or even from men, but as possessors of "happiness" (cf. the Authorized Version of Joh_13:17, and frequently). It describes them in reference to their inherent state, not to the gifts or the rewards that they receive. -Pulpit commentary

I have never liked the expression "be blessed;"  I think it's because it suggests that it's something I have to allow or receive, a sort of "work" to be done.   But as the Pulpit Commentary suggests it is an "an inherent state"---I am blessed, and it is more a matter of realizing or recognizing it, not receiving it.
A great relief.

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Mat 5:2-3  And he opened his mouth and taught them, saying: “Blessed are the poor in spirit, for theirs is the kingdom of heaven."

 In spirit; Matthew only --Pulpit

Luk 6:20  And he lifted up his eyes on his disciples, and said: “Blessed are you who are poor, for yours is the kingdom of God."

The first Beatitude is the sum and substance of the whole sermon. Poverty of spirit stands in contrast to self sufficiency (Rev_3:17) and as such is perhaps the quality which is most of all opposed to the Jewish temper in all ages (cf. Rom_2:17-20). -Pulpit Commentary

Rev 3:17: For you say, I am rich, I have prospered, and I need nothing, not realizing that you are wretched, pitiable, poor, blind, and naked.

Romans 2:17-21: But if you call yourself a Jew and rely on the law and boast in God and know his will and approve what is excellent, because you are instructed from the law; and if you are sure that you yourself are a guide to the blind, a light to those who are in darkness, an instructor of the foolish, a teacher of children, having in the law the embodiment of knowledge and truth— you then who teach others, do you not teach yourself?

In the first five chapters of his book, Isaiah indicts the people of Judah and the surrounding nations, saying, "Woe unto you and you and you." But in chapter 6, when he saw the Lord high and lifted up, he said, "Woe is me!" When Peter realized who Jesus was on a boat in the Sea of Galilee, he said, "Depart from me; for I am a sinful man" (Luk_5:8). When John the revelator saw Jesus, he fell down as though he were dead (Rev_1:17) -Jon Courson

Fourfold:
There must be emptiness before there can be fullness, and so poverty of spirit precedes riches and grace in the kingdom of God.