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"Whereby shall I know that I shall inherit it?"
Avraham’s words are very challenging. The Gemara (Nedarim 32A) speaks very critically about this:
Rabbi Abahu said in the name of Rabbi Elazar: Why was Avraham our forefather punished, and his children enslaved in Egypt for two hundred and ten years? … Shmuel said: Because he went too far in testing the attributes [i.e., the promises] of the Holy One blessed be He, as it is written, "Whereby shall I know that I shall inherit it? "
According to the Gemara Avraham was punished in the wake of this doubt in faith, and as a result the people of Israel were enslaved in Egypt.
However, this interpretation is problematic, since two verses earlier, we have seen the immense faith Avraham shows. Avraham is an old man, and the Holy One, blessed be He, makes him a promise:
"And behold the word of the Lord came to him, saying: ‘This man shall not be your heir; but he that shall come forth out of your own bowels shall be your heir."
And the Torah goes on to tell us how on receiving this promise testifies that Avraham fully believed:
And he believed in the Lord and He counted it to him as righteousness.
Indeed, the Gemara (Megillah 31B) explains the verse, "Whereby shall I know that I will inherit it?" in another way:
And he said, O Lord God, Whereby shall I know that I shall inherit it. Said Abraham before the Holy One, blessed be He: Master of the Universe, perhaps God forbid, Israel will sin before Thee and Thou wilt do to them as Thou didst to the generation of the Flood and the generation of the Division? He answered, Not so. He then said before Him: Master of the Universe, by what shall I know this? He said: Take me a heifer of three years old etc.
Avraham did not waver in his faith in God. Avraham feared that the nation of Israel would sin and thereby lose the Land of Israel, so he asked, "Whereby shall I know?" How can I know that the Nation of Israel will merit having the land of Israel?
According to this, the difference between the two promises was that when the promise was made regarding his offspring, Avraham was certain that the promise would be fulfilled because it depended on God alone. But when the promise involved the inheritance of the Land of Israel, Avraham knew that the inheritance of the Land of Israel depended on the actions of the people of Israel, and he was apprehensive about this. Avraham knows that that if Israel sins, God forbid, the land may eject them: "that the land vomit not you out also, when ye defile it, as it vomited out the nation that was before you." (Leviticus 18:28).
And what is God’s response?
We will not now enter into all the details of the vision of the Covenant of the Pieces, but one thing is clear: God makes an covenant with Avraham and in this manner tells him that indeed the people of Israel will sin and be exiled and punished, but the people of Israel will return to the Land of Israel: "And in the fourth generation they shall come back hither; for the iniquity of the Amorite is not yet full". There is a covenant between the people of Israel and God, and this covenant is eternal. Even if the people of Israel sin, in the end they will return to Israel. 1
The Gemara in Megillah (ibid.) also explains that God offers us the consolation that through the Nation of Israel offering sacrifices, or even by merely reciting the order of sacrifices, God will forgive them:
He then said before Him: Master of the Universe, This is very well for the time when the Temple will be standing, but in the time when there will be no Temple what will befall them? He replied to him: I have already fixed for them the order of the sacrifices. Whenever they will read the section dealing with them, I will reckon it as if they were bringing me an offering, and forgive all their iniquities.
We can go even further. There is really no contradiction between "And he believed in the Lord" and "Whereby shall I know that I shall inherit it?" Even a person who believes with perfect faith sometimes feels difficulties. Sometimes a person can be helpless and say, "I will lift up my eyes to the hills; from where will my help come?" However, immediately afterwards he will know to say, "My help is from the Lord, the maker of heaven and earth."
Simply put, the Nation of Israel will return to its land once the Amorites will be so saturated with sins that they will not be entitled to remain in Israel. However, it is possible to understand the verse "And in the fourth generation they shall come back hither;" as follows: the people of Israel will in the future return to God, through repentance, and will in any event return to the Land of Israel. (This may perhaps be dependent on a dispute among the Amorites [Talmudic sages] whether the Nation of Israel will be redeemed in any event, or whether their deliverance will occur only after repentance).

Kuzari -Rabbi Ari Shvat Kuzari class 8- "Answering Questions on the Kuzari's Proof from Mass Revelation
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