Ramban #1 (citing the Ibn Ezra): He meant 'Does it produce grain and fruit'?

Ramban #2: Even assuming that it is a good land (Refer to 13:19:1:3), there are some countries that produce luscious fruit ¹ that require a lot of rain, raking and fertilizing, to prevent the fruit from drying-up, whereas others, which are inherently dry, produce dry fruits, ² , which keep longer than their more juicy counterparts. ³

Ramban #3 (citing Targum Onkelos ⁴ ): He instructed them to find out whether the people were inherently wealthy or whether they need to come on to their neighbors, in spite of the fact that the land is good.

Ramban #4 (in Pasuk 22): He wanted the spies to inform the people how, in spite of the age of Chevron, ⁵ it was still producing such luscious fruit - how much more so cities that were built later.

Seforno and Targum Onkelos ⁶ : He meant 'Is the land fertile or is it lean?' ⁷

Rashbam: He meant that the spies should let Yisrael know that the land was flowing with milk and honey, as Hakadosh-Baruch-Hu had promised them. ⁸ 7. Targum Yonasan: He meant 'Is the fruit luscious or meager'?

Oznayim la'Torah: Because here he was referring to the natural state of the land - whether it is fertile of not - which is best guaged where nobody lives, whereas in the previous Pasuk he was referring to the state of the land after it has been tilled by its inhabitants. ¹

Oznayim la'Torah: In Pasuk 18, with reference to the mountains (mentioned in Pasuk 17) - rocky terrain which is generally designated for sheperding sheep; in Pasuk 19, with reference to the fertile lowlands, which are designated for farming, and Pasuk 20, the deep valleys, which are near the sea,and which, due to the water tht flows into them from the mountains and to the sea-air, are the most fertile of all. ¹

Rashi: He asked whether there was a Tzadik ¹ there whose merits would shield over the people. ²

Seforno and Targum Yonasan: He was simply asking whether the land contained fruit-trees. ³

Bava Basra, 15a: He instructed them to see whether the person whose years are (long) like a tree ⁴ and who shielded over his generation like a tree - with reference to Iyov ⁵ - was still alive.

Ramban, Rashbam and Seforno #2: It means that they should strengthen themselves ¹ and take some of the local fruit ² to bring back with them to show the people. ³

Seforno #1 and Targum Yonasan: It means that they should make a Chazakah on the land ⁴ by taking some of its fruit. ⁵

Oznayim la'Torah: Moshe wanted them to bring back fruit of Eretz Yisrael, not only to show the people the amazing quality of the fruit, but also in order to take T'rumos and Ma'asros from it. ⁶

Rashbam: The Torah tells us this as an introduction to the bunch of grapes to which it refers in Pasuk 23. ¹

Targum Yonasan: Because grapes begin to ripen on the twenty-ninth of Sivan - to teach that the spies returned forty days later on the eighth of Av, ² the day before the night of Tish'ah be'Av. ³