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These verses lead us to ask: What exactly is it that makes the land of Israel so praiseworthy in the eyes of the Torah?
Rashi explains: "In the land of Egypt, you had to bring water from the Nile on foot in order to irrigate it; you had to lose sleep, to toil. The lowlands were irrigable, but not the highlands, and you had to bring the water up from the low areas to the high ones. But with this, 'by the rain of the skies you will drink water.' You can sleep in your bed while the Holy One, may He be blessed, irrigates lowland and highland, open and enclosed areas alike." This, then, is what makes the land of Israel so praiseworthy: Rain falls everywhere, and therefore one need not labor as they do in the land of Egypt.
Rain in Israel (17)
Rabbi Uzi Kalchaim zt"l
1 - Earth's Eyes to Heaven
2 - The Three Keys
3 - Balance
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"According to the plain meaning of the text, what we have here is a warning. [God] said to them, Keep all of the commandments and you shall inherit a land flowing with milk and honey, for God will provide rain for your land in its proper time, and the land will yield fruits. But you must know that [this land] is not like the land of Egypt, which can be irrigated by foot from the rivers and lakes, as a garden of vegetables; rather, it is a land of hills and valleys, and drinks water from the rain of the skies, through no other means. It demands God's constant providence for rainfall, for it is a very thirsty land and needs rain all year long. If you violate the will of God and He does not provide it with abundant rain, the land is very bad. You shall not succeed in sowing it, and you shall not cause it to blossom; not so much as a blade of grass shall sprout on its mountains."
In the land of Israel the blessing does not flow naturally in the rivers and does not depend solely upon human toil, upon the amount of effort one puts into digging channels from the rivers. Rather, there is a dependency upon rain for irrigating the land. There is a dependency upon heavenly showers, from above, as it is written in the second paragraph of the Shema (Deuteronomy 11:13-21). These verses teach us that there is an interdependence between spiritual-moral integrity ("Be careful that your heart not be tempted to go astray") and the promise of abundant rainfall ("I will grant the fall and spring rains in your land"). In the land of Israel one must constantly be aware of God's providence because it is a land dependent on rainfall, and if you violate God's will, He will not provide you with sufficient rain. This land, then, as such is very bad. It will not bear fruit if you are sinful.
The Ramban continues: "It would be easy enough for the Almighty to destroy the inhabitants of Egypt, to dry up their rivers . . . but the land of Canaan could be destroyed even quicker [if the Almighty decided] not to provide it with rain. A sick person is more in need of merit and prayer for God to heal him than a healthy person is for God to keep him from being visited by illness."
A sick person, because he lacks the protection that nature usually provides, needs special merit in order to be healed. He needs "advocates" to come to his defense, for example, repentance and virtuous deeds. Therefore, he is in need of divine favor because he has left the normal protective framework. The sages hence teach, "The divine presence hovers over the head of the ill" (Shabbat 12b), for he has left the natural order, nature's protection. They also teach, "A person must always request divine mercy in order to keep himself from becoming ill, for if he becomes ill he is told, 'Show your merits and be exempted.' "
This, then, lies at the foundation of our request for rain in the land of Israel. We do not receive the blessing naturally. Rather, we must ascend spiritually and morally, to pray to God in order to merit the blessing of rain. Among the four reasons brought in the Midrash (Bereshit Rabba 13:9) for God's decision to have the earth "drink only from above" (i.e., be irrigated by rain rather than flooding, etc.) is "in order that all people raise their eyes to heaven."
When praying, a person lifts his eyes to heaven and improves his ways on earth in order to merit rain. This is what makes the land of Israel so great: It is not irrigated in a manner that feeds our baser instincts. It does not allow us to enjoy bounty in a simple manner. Rather, it awakens within us the longing and expectancy needed for praying for rain. In this manner, our practical lives are sanctified by the bond between heaven and earth.

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Based on Siach Shaul, Pirkei Machshava V’Hadracha p. 263 (address at the laying of the cornerstone of the Yeshiva Chakla’it in Kfar Haroeh)
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