Moshe's intent was not to evaluate whether it is a worthwhile land. Rather, the focus was still the how, of how to best conquer the land. Different types of land, populations, and towns require different types of military campaigns. To turn quickly to sefer Devarim, perek 1, this is expressed well as:
They need to know by which way they must go up. To this end, there is not really a wrong answer. They might be strong or weak, and depending on that, they might need a greater or lesser fighting force. The land might be good or bad in terms of being able to support the army's needs as they fought. If they live in strongholds, they might need prolonged sieges. One can of course spin any of these answers towards negative, and the midrash highlights how the spies spun all the positives into negatives. Thus, the land consumed its people. But really it was Hashem letting them pass by without notice. This is a way of emphasizing just what it is the spies did.
| כ וּמָה הָאָרֶץ הַשְּׁמֵנָה הִוא אִם-רָזָה, הֲיֵשׁ-בָּהּ עֵץ אִם-אַיִן, וְהִתְחַזַּקְתֶּם, וּלְקַחְתֶּם מִפְּרִי הָאָרֶץ; וְהַיָּמִים--יְמֵי, בִּכּוּרֵי עֲנָבִים. | 20 and what the land is, whether it is fat or lean, whether there is wood therein, or not. And be ye of good courage, and bring of the fruit of the land.'--Now the time was the time of the first-ripe grapes.-- |
The instruction to bring back fruit shows a desire for the land of their forefathers, the land promised by Hashem. Also, to backtrack a bit from what I wrote above, maybe the point of this as well as all the questions was to conclude how good Hashem's gift was going to be, rather than assessing how to best acquire it.
The point of mentioning that it was the time of the first-ripe grapes is that this is what they will bring back, and what will perhaps lead to the naming of Eshkol.
Next,
The statements in pasuk 22 are written for an audience with a knowledge of the outside world. That is, Tzoan Mitzrayim is something they would know, and serves as a point of reference, to explain that Chevron indeed exists at this point. So too these children of Anak, mentioned by name, would make an impression in the eyes of the reader.
Interestingly, this Jewish Encyclopedia article lists Achiman, Shashai and Talmai not as individuals, but as clans. Perhaps.
Anak might mean giants, in the sense of really tall people. See pasuk 33 below.
Next,
If it only got its name from the Eshkol they brought back, then it was called the valley of Eshkol in pasuk 23 al shem sofo. The confounding issue, which need not be an issue at all, is that one of the Baalei Bris Avraham was Eshkol. Bereishit 14:
| כד בִּלְעָדַי, רַק אֲשֶׁר אָכְלוּ הַנְּעָרִים, וְחֵלֶק הָאֲנָשִׁים, אֲשֶׁר הָלְכוּ אִתִּי: עָנֵר אֶשְׁכֹּל וּמַמְרֵא, הֵם יִקְחוּ חֶלְקָם. {ס} | 24 save only that which the young men have eaten, and the portion of the men which went with me, Aner, Eshcol, and Mamre, let them take their portion.' {S} |
See this parshablog post, and Midrash Rabba, and Gra. None of this is necessary, since who says that this was ever named after Eshkol?
וּמִן-הָרִמֹּנִים might be the basis for claiming the enormity of the Rimon, in a midrash, such that 12 spies were able to hide in it:
"The daughter of Anak had gone into her father's garden and taken a pomegranate, which she ate, after having peeled off the skin and cast it aside. Then the twelve spies came and, seeing her father, were struck with fear and hid themselves under the pomegranate-skin, believing it to be a cave. The daughter of Anak in the meantime came back and, seeing the pomegranate-skin still lying there, was afraid lest her father might scold her for lack of neatness. She therefore took the pomegranate-skin, with the twelve spies hidden therein, and cast it out of the garden, noticing the weight added by the men no more than if the skin had been the shell of an egg."They say in Jewish Encyclopedia to check out The Giant's Toy (or The Giant's Daughter) for a striking comparison.
Next,
| כה וַיָּשֻׁבוּ, מִתּוּר הָאָרֶץ, מִקֵּץ, אַרְבָּעִים יוֹם. | 25 And they returned from spying out the land at the end of forty days. |
Forty days might be a canonical number, meaning a lot of days, similar to the number of years certain Shofetim presided. But look to the next perek and we see that it is taken literally and precisely.
| לד בְּמִסְפַּר הַיָּמִים אֲשֶׁר-תַּרְתֶּם אֶת-הָאָרֶץ, אַרְבָּעִים יוֹם--יוֹם לַשָּׁנָה יוֹם לַשָּׁנָה תִּשְׂאוּ אֶת-עֲוֹנֹתֵיכֶם, אַרְבָּעִים שָׁנָה; וִידַעְתֶּם, אֶת-תְּנוּאָתִי. | 34 After the number of the days in which ye spied out the land, even forty days, for every day a year, shall ye bear your iniquities, even forty years, and ye shall know My displeasure. |
Rashi considers whether 40 days is possible:
| They returned from scouting the Land at the end of forty days: But does not the Land measure four hundred parasangs by four hundred parasangs [a parasang is equivalent to about three-and-a-half miles in length], and an average person’s daily traveling distance is ten parasangs? Thus, it takes forty days to walk from east to west, and they traversed its length and its breadth? However, since it was revealed before the Holy One, blessed is He, that He would sentence them with a year for every day, he shortened the way [so they covered ground more rapidly]. — [Mid. Tanchuma 8] | וישבו מתור הארץ מקץ ארבעים יום:והלא ארבע מאות פרסה על ארבע מאות פרסה היא, ומהלך אדם בינוני עשרה פרסאות ליום, הרי מהלך ארבעים יום מן המזרח למערב והם הלכו ארכה ורחבה, אלא שגלוי לפני הקב"ה שיגזור עליהם יום לשנה, קצר לפניהם את הדר |
I don't know enough about the geography of Eretz Yisrael. But perhaps they split up to cover more ground?
Next:
Seeing is believing, is experiencing. This was what Moshe requested. And it is a way of showing that Hashem's promise of a fertile land is true -- it is a land flowing with milk and honey.
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