Why did the spies make a point of mentioning Amalek, who was not even one of the seven Cana'ani nations?
Rashi: Because, since they had already been scalded by Amalek once, 1 they mentioned Amalek (a southern neighbor of Cana'an) in order to frighten them.
As the old saying goes 'Once bitten, twice shy!'
Why did they mention specifically the nations that they did and the four areas where they lived?
Rashi: They mentioned that the mighty Cana'ani nation lived beside the River Yarden, to intimate that they would not even be able to cross into Eretz Cana'an to begin the conquest of Cana'an.
Ramban: They mentioned these mighty nations, who lived in the four areas mentioned, to convey the message 1 that there was no point from which Yisrael would safely be able to attack them without suffering defeat.
Ramban: Initially they only hinted, and did not say it outright, because they were afraid of Moshe and Aharon.
Why did they omit the answer to the question "ha'Me'at hu Im Rav" and "ha'Tovah hi Im Ra'ah"?
Ramban: Because at the outset they planned to say to the people directly "Eretz Ocheles Yoshvehah", indicating that the people were few, but exceptionally strong.
Here the Torah writes that Amalek was in the south and the Cana'ani by the sea, But later, in 14:45, it writes "Vayered ha'Amaleki ve'ha'Cana'ani ha'Yoshev ba'Har", implying that also Amalek was situated in the mountains?
Refer to 14:25:151:1 & 14:25:152:2 and note.
Here the Torah writes that Amalek lived in the south and the Cana'ani by the sea. But later, in 14:25, it writes "ve'ha'Amaleki ve'ha'Cana'ani Yoshev ba'Eimek"?
Refer to 14:25:151:2 & 14:25:152:2 and note.
