What are the connotations of "u'Mah ha'Aretz asher Hu Yoshev bah, ha'Tovah hi Im Ra'ah"?
Rashi: Does the land possess fountains and good healthy deep-water springs?
Ramban #1 (citing Ibn Ezra): Is the air good and is the water drinkable.
Ramban #2: Is it in general, a good land that produces a lot of fruit, or a bad one (incorporating good and luscious produce of all kinds).
Ramban #3 (on Pasuk 2): If the land was bad,
they would leave it for later and first capture the parts that were good.
Which Moshe said with reference to "ba'Negev" in Pasuk 17.
We see that, when it came to the crunch, Yehoshua did not capture all the areas of the land.
What are the connotations of "ha'Bemachanim Im be'Mivtzarim"?
Rashi (citing Targum Onkelos) and Targum Yonasan: He meant to ask whether they lived in open cities or in fortified ones.
Ramban (Ibid.): If they lived in fortified cities, they would need to prepare ramparts to capture them or to attack from a different direction.