1)

Why does it mention leading Yisrael in the Midbar for 40 years?

1.

Radak: You did not lack anything then. I habituated you to My Chukim, lest you learn from the Chukim of Eretz ha'Emori when you come to inherit it.

2.

Malbim: There were repulsive thoughts in Yisrael's hearts that they learned from the Egyptians. Hashem could not bring them immediately to Eretz ha'Emori, lest they return to do like the abominations of Egypt ? "Ki Atem Yedatem Es Asher Yashavnu b'Eretz Mitzrayim?; va'Tir'u Es Shikutzeihem?" (Devarim 29:15-16). Therefore, he led them for 40 years in the Midbar, until the previous generation died out, and the new generation saw Hashem's deeds and Hashgachah, and were refined in the Midbar. This was preparation lest you sin with idolatry, Arayos and the abominations of Egypt and Kena'an!

2)

Did Hashem lead Yisrael in the Midbar to inherit Eretz ha'Emori?

1.

Radak #1: I habituated you to My Chukim in the Midbar, lest you learn from the Chukim of Eretz ha'Emori when you come to inherit it.

2.

Radak #2: "Lareshes Es Eretz ha'Emori" refers to the Reisha ? it is why I raised you from Egypt.

Sefer: Perek: Pasuk:

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