Gemara: What does it mean, "…that the first ones gave the boundaries" (Devarim 19:14)? Rav Shmuel bar Nachmani said: That which it says, "These are the sons of Se’ir the Chorite, the settlers of the land" – does it mean that others sit in the sky?! Rather it means that they were experts in settling the land, for they would say that the place where this measuring stick is found is good for an olive tree; the place of this stick is for grapes; the place of this stick is for a fig tree.
Ein Ayah: People’s connection to the land must be entrenched well in the beginning. At the time that those who have the characteristics to connect their most internal part of their lives to the land appear on the stage of history, it is important that no matter of spirituality hold them back. For it is only when there is a total dedication to matters of the land that a man will be prepared to penetrate into the depths of knowledge with a sense of the internal spirit to know the ways of the land and its life. He can thus be connected in a manner that is appropriate for one who was meant to "work the earth from which he was taken" (see Bereishit 3:23).
These were the first people – people upon whom the higher spirituality of Torah did not shine. They were able to be absolutely linked to the land; they were the "settlers of the land." The depth of the connection and the internal desire for the land was what brought about the penetration and the knowledge of the land’s qualities and the ability to create the first foundations for supporting the land and using it to develop its cultivation. They were able to determine which land was right for olives and which for grapes and which for figs.
Their total dedication to the land and deep connection to it caused them to have a sharp, internal and personal connection to it. It was not just a quick scan of what was needed to work the land that they possessed. Rather, since their senses were focused on it, they reached the deepest, most individual knowledge, so that they knew how to maximize the plantings. They understood the needs of olives, grapes, and figs, each according to its value. This definitely applied to the lower plants, such as grain and legumes, and the like, which are the basis of physical life.
This lower culture of mankind, as a species that cultivates and is sustained by the earth, preceded the light of Torah. In this way, the higher form already would find its strong basis in the fabric of society, upon which it can rest. The society of the land settlers needed to precede the Torah society chronologically, before the heavenly light appeared. "You have seen that I have spoken to you from the heavens" (Shemot 20:19). The people of the land, who are imbedded in the land with all of their life senses, have their spirituality leaning toward physical beauty, the happiness of the flesh, and the pleasure of the senses. The olive makes the face shine (Tehillim 104:15) – the realm of beauty. The grape is related to man’s happiness (see ibid.). The fig is the source of a type of honey, which is most beloved by one’s taste buds, which is so important to people.
More than any other, people are most concerned about grapes, because drunkenness connects physical happiness to excited imagination, so that one is ready to be motivated by other physical pleasures. That is why olive and fig are written in singular and grapes are written in plural. Indeed, many are interested in there being as many grape orchards as possible