In the said video Hazony makes the following interesting claims:
(1) God has commanded Adam and his descendants to toil and be involved agricultural work, while the land produces only thorns and thistles.
(2) Cain is the more pious of the two brothers: he obeys God's decree (1) and it's his idea to bring sacrifices.
(3) Cain is the archetype of the submissive mankind, that makes dictators and the like (I believe Ayn Rand would have named him 'collectivist')
on the other hand
(4) Avel (Abel) is the shepherd, who, using his intelligence leads an easier life.
(5) He refuses to follow Gods decree (1) and has his herds do the work for him.
(6) Avel is the archetype of the individualists, who break away from submissive societies, while also promoting and bringing blessed change to mankind.
(7) God likes Abel types, more that Cain types.
I would like to challenge some of these claims in order to present a broader view of this and other Biblical narratives.
Cain and Able are the archetypes of other brotherly relationships we find in the Torah . Consider: Isaac and Ishmael; Jacob and Esau; Joseph and Judah (and other siblings); Moses, Aharon and Miriam. In all the said cases we witness a brotherly quarrel, usually violent , and one side usually chosen over the other. The question that the disputing siblings are trying to resolve is: "who continues the legacy of the father or the previous generation".
What is Adam's legacy?
According to Hazony (1), God commanded Adam and his descendants to toil. Let's read the passage in its context:
And YHWH Elohim said unto the serpent: 'Because thou hast done this, cursed art thou from among all cattle, and from among all beasts of the field; upon thy belly shalt thou go, and dust shalt thou eat all the days of thy life.
And I will put enmity between thee and the woman, and between thy seed and her seed; they shall bruise thy head, and thou shalt bruise their heel.'
Unto the woman He said: 'I will greatly multiply thy pain and thy travail; in pain thou shalt bring forth children; and thy desire shall be to thy husband, and he shall rule over thee.'
And unto Adam He said: 'Because thou hast hearkened unto the voice of thy wife, and hast eaten of the tree, of which I commanded thee, saying: Thou shalt not eat of it; cursed is the ground for thy sake; in toil shalt thou eat of it all the days of thy life. Thorns and thistles shall it bring forth to thee; and thou shalt eat the herb of the field. In the sweat of thy face shalt thou eat bread, till thou return unto the ground; for out of it wast thou taken; for dust thou art, and unto dust shalt thou return.'
Just as with the serpent and the woman, there is no divine command to toil and grow 'thorns and thistles'. But rather it's a punishment, a curse if you will. God describes the state of affairs from this point onward. However, we don't believe that God is vindictive. His punishments are instructive and are means to correct Adam's sin. How do Adam's children approach the situation.
Let's understand the meaning of their names (they are archetypes after all).
Cain's name is explained during his birth:
And the man knew Eve his wife; and she conceived and bore Cain, and said: 'I have gotten (קָנִיתִי kaniti) a man with the help of (or together with) YHWH.'
The word קָנִיתִי is translated to gotten. However, in the Biblical language, the word carries a combination of meanings: acquire, establish, create. Cain's name carries a hint of power, achievement and self-fulfillment through accomplishment. He see's God's punishments as merely technical challenges and obstacles to be overcome. He doesn't stop and ponder at their meaning, to decipher God's message. The sacrifice he offers is actually an act of defiance, showing his ability to overcome the Earth's curse by technical means.
Abel's ( hevel הבל) name is not explained, but it is usually translated as vanity, as in the book of Ecclesiastes:
Vanity of vanities (havel havalim), saith Koheleth; vanity of vanities (havel havalim), all is vanity (hevel).
What profit hath man of all his labor wherein he laboureth under the sun?
One generation passeth away, and another generation cometh; and the earth abideth for ever
The term hevel is applied to everything that is passing. Abel's approach – derived from the Biblical perception that being is fluid  – is that man's efforts are vain, and achievement is always temporary. He adopts the life of a shepherd, which doesn't require attachment to the earth. it also leaves him more time for pondering the meaning of life and understanding God's message. Abel's is not an inventor but a philosopher, and contrary to Hazony's statement (2), it's he who is the pious and moral of the two siblings. Unlike Cain, his sacrifice is an act of submission and humility.
God's punishments were meant to create dissatisfaction with the material world, and thus help man look beyond his immediate existence. While Abel understands their real meaning, Cain disregards them. When Cain's offering has been rejected, he once again saw a "technical" problem, of having a competitor, and his action removed him.
This time, God's punishment was more direct and He once again repeated and worsened Cain's situation – in order to force him to become a nomad. However, Cain settled down and built a city.
So is this all to it? God prefers the humble thinker over the ever-sinning accomplisher?
When I studied the case of Jacob and Isaac, I arrived at the conclusion that when two quarreling siblings are advocating apposing worldviews, the desirable solution is actually a synthesis of the two approaches. Although one is not utterly correct while the other is completely astray, eventually one brother is chosen over the other. This is because that just at the present, when no synthesis is possible, he is a better choice for promoting God's plans . In our story, Abel's pondering approach was more appropriate than Cain's reckless storming.
After disregarding Cain's sacrifice, God still approaches him:
And YHWH said unto Cain: 'Why art thou wroth? and why is thy countenance fallen? If thou doest well, shall it not be lifted up? and if thou doest not well, sin ; and unto thee is its desire, but thou mayest rule over it.'
What God tells Cain, that just as he tried to overcome God's punishments, he should overcome his tendency to sin. It is a though he should tame that "coucheth at the door" just as he tried to tame the land. There is also a subtle hint that Cain may have a higher standing than Abel.
How is it that Cain is the greater of the two brothers?
Of the two siblings, only Cain is capable of building a lasting civilization. History teaches us that the civilizations emerged where wide-scale agriculture was possible. Consider the Nile, Euphrates, Tigris, Ganges and Yangtze rivers (note that the first three rivers are flowing from Eden). The agricultural revolution made it possible to feed large populations and have a significant portion of the people who are involved in cultural advancement which is not bent on immediate survival .
When Cain murdered Abel, he halted society's moral progress. His descendants continued the technical and political progress but they grew increasingly violent. Although moral thought has reemerged in Seth's lineage (note how his offspring's' names are similar to those in Cain's lineage, as though they are providing a moral counterpart to the technical achievement), it was too late, and Cain's society is to be wiped out in the flood.
And the earth was corrupt before Elohim, and the earth was filled with (violent) robbery. And Elohim saw the earth, and, behold, it was corrupt; for all flesh had corrupted their way upon the earth.
Cain's progeny became filled with robbery. Lacking Abel's philosophy of detachment, they became addicted to technology and possessions.
Hazony is correct in asserting that shepherds are less threatened by society's suppression. Indeed, when society becomes corrupt, fleeing to the desert becomes a reasonable option:
Oh that I were in the wilderness, in a lodging-place of wayfaring men, that I might leave my people, and go from them! For they are all adulterers, an assembly of treacherous men. (Jeremiah Ch. 9) 
However, by themselves, shepherds, haven't left a significant mark on history. They live on the outskirts of society and thus outside of history.
Hazony is also correct in stating that the founding figures of Israel were shepherds, and their legacy is to be found in Judaism. The shepherd is the antithesis of a corrupt urban society. Abraham, stood against the pagan civilizations of his time. When the Israelites were freed from Egyptian bondage they were required to eat unleavened bread – in the manner of desert wanderers who have no time to wait for the dough to leaven – the opposite of Egypt . Moses received his first revelation when he fled Egypt and adopted a shepherd's lifestyle. However, the only reason these individuals gained worldwide attention and left a historical mark was because their descendants organized themselves in an agricultural society in the land of Canaan . This was Abraham's promise:
'As for Me, behold, My covenant is with thee, and thou shalt be the father of a multitude of nations. Neither shall thy name any more be called Abram, but thy name shall be Abraham; for the father of a multitude of nations have I made thee. And I will make thee exceeding fruitful, and I will make nations of thee, and kings shall come out of thee. (Genesis, Ch. 17)
This not just a favor God makes for Abraham. This is the only way to bridge the Cain and Abel gap, and thus bring blessing to mankind. The Biblical utopian civilization combines both Cain's technical approach with Abel's moral investigations into the deeper meaning of existence. It enjoys the fruits of technology and science, while it also teaches that true satisfaction and happiness are found in moral and spiritual achievement.
 The traditional approach to the first chapters in Genesis is that they conceal secret knowledge, and help focus the readers mind to deeper truths.
 If the Torah is not explicit in mentioning violence, the Sages readily add midrashic details to show that violence had occurred.
 see discussion here
 I believe this approach can be found in Rabbi Yoel Bin-Nun's lesson here
 Rabbi Bin-Nun interestingly connects the agricultural revolution with the expulsion from Eden, see here
 Social and religious corruption may have also caused Jonadav son of Rechab to become a tent dweller:
'We will drink no wine; for Jonadav the son of Rechab our father commanded us, saying: Ye shall drink no wine, neither ye, nor your sons, for ever; neither shall ye build house, nor sow seed, nor plant vineyard, nor have any; but all your days ye shall dwell in tents, that ye may live many days in the land wherein ye sojourn… therefore thus saith YHWH of hosts, the Elohim of Israel: There shall not be cut off unto Jonadab the son of Rechab a man to stand before Me for ever (Jeremiah Ch.35)
In his time, the Prophet's (secret) society (who were headed by Elijah) also fled to caverns, in fear of Jezebel's prosecutions.
 Besides the unleavened bread I believe some more commandments can be explained in terms of recalling the shepherd legacy: the Pesach lamb; shatnez (mingled garment); kashrut; Lunar months.
 Ironically this was sometimes involved in battling corrupt shepherd tribes who wouldn't produce but rather rob farmers, see Judges Ch.6:
And so it was, when Israel had sown, that the Midianites came up, and the Amalekites, and the children of the east; they came up against them; and they encamped against them, and destroyed the produce of the earth, till thou come unto Gaza, and left no sustenance in Israel, neither sheep, nor ox, nor ass. For they came up with their cattle and their tents, and they came in as locusts for multitude; both they and their camels were without number; and they came into the land to destroy it.