What are the connotations of "Lech Na Re'eh"?
Chulin 91b: 'It teaches us that Yosef left at an hour when one could see - to teach us that a Talmid-Chacham should not go out alone at night. 1
See Torah Temimah, note 15.
What was the purpose of Yosef's mission?
Moshav Zekenim, Hadar Zekenim (to 37:13): To instruct the brothers to leave Shechem, due to danger. 1
Seforno: His father sent him to rectify anything regarding the shepherding that needed to be seen to. 2
Ohr ha'Chayim, Malbim: It was simply to find out the well-being of his brothers and return to tell Yaakov, like the verse says. Because also his return was part of the mission, the guarantee 'a Shali'ach Mitzvah is not harmed' applied also to his return, according to all opinions.
Also see 37:13:153.
What is the significance of the fact that Yaakov sent Yosef from "Emek Chevron"?
Ramban: The Pasuk is pointing out that the place from which Yaakov sent him was far 1 from where the brothers were stationed; a. which explains why they were able to do him harm (something that they would not have dared to do in the vicinity of their father); b. which highlights Yosef's righteousness, inasmuch as he was willing to travel far even though he knew that the brothers hated him. 2
Bearing in mind that Chevron is built on a mountain (as Rashi proves), why does it say that Yaakov sent Yosef "from Emek (the valley of) Chevron"?
Rashi and Ramban #1 (citing Midrash Rabah 84:13): The Pasuk is hinting at 'the Etzah Amukah' 1 to the Tzadik who was buried in Chevron (i.e., Avraham).
Ramban #2: The Pasuk is pointing out that the place from which Yaakov sent him was far from where the brothers were stationed. See above, 37:14:1.1:1 .
Moshav Zekenim, Seforno: Yaakov accompanied him as far as the valley of Chevron (the bottom of the mountain), at which point he sent him on his way. 2
Divrei David: I.e., Hashem's word and plan. Namely, "Your children will be strangers in a foreign land" (Bereishis 15:13) (Rashi). Yaakov acted under the Divine influence. Normally, one would never send his beloved child to a dangerous place! (Malbim)
Moshav Zekenim: Yosef told Yaakov, 'Go back!' (you need not accompany me). Yaakov taught him about Eglah Arufah (that having an escort protects. See Rashi to Devarim 21:7). This was the Halachah that Yosef remembered, and hinted to his father - refer to 45:27:1:1 and notes.
We know that he was headed to Shechem! Why does it say "he arrived in Shechem," and not simply 'he arrived there'?
Rashi: Because Shechem would prove to be a location of punishment. 1
Rashi: There Yaakov's sons sinned, there Dinah was afflicted, and there the kingdom of David was split into two (see Melachim I 12). Divrei David - Even though they sinned in Dosan, they counseled to do so in Shechem.
QUESTIONS ON RASHI
Rashi writes: "'From the valley of Chevron' - But Chevron was in the mountains, as in the verse, 'They ascended the Negev, and he came until Chevron' (Bamidbar 13:22)!" How does that verse prove anything? Perhaps when the spies entered Eretz Yisrael from the wilderness, the word "ascended" is used in the sense that Eretz Yisrael is higher than all other lands (see Rashi to 45:9)?
Gur Aryeh #1: That verse says, "ascended... and came until Chevron;" which implies that that entire segment of their journey was an ascent, from Kadesh Barnea until Chevron. 1
Gur Aryeh #2: We can offer other proofs that Chevron is a mountain - a. Rashi (to Bamidbar 13:22) writes that Chevron is rocky terrain; and that it why it was relegated for burial ground; b. We also derive that Chevron is a mountain from Yehoshua 14:12-13; Kalev asks for "this mountain," upon which Yehoshua grants him Chevron.
Topographically, the Chevron region is in fact the high point along the mountain ridge that runs down the center of Eretz Yisrael. Chevron lies at an altitude of 900m above sea level. (The spies presumably came via Be'er Sheva, which is only at 300m). Nevertheless, note that there is a valley in Chevron, which is located between the hill of the city itself (Tel Rumeida) and the opposite hill with Me'aras ha'Machpelah at its foot. Perhaps this is Emek Chevron in the simple meaning of the verse. Compare to 37:14:2:3. (CS)
Rashi writes: "He came to Shechem - a place pre-destined for misfortune." Why interpret this way?
Gur Aryeh: Yaakov already said that Yosef was to find his brothers in Shechem (37:13); so our verse could have sufficed to say, 'he came there.' The word Shechem is extra for interpretation.
Rashi writes: "Shechem - a place pre-destined for misfortune." But Yosef was later sold in Dosan (37:17), not in Shechem!
Gur Aryeh: Refer to 37:17:152.1:1.