Why does the Torah repeat here what it already told us in Toldos (see Bereishis 28:5)?
Rashi: Because it interrupted the story of Yakov to describe Esav's reaction. 1
Targum Yonasan: The Torah hints at five miracles 2 that happened to Yakov - that we would not have been able to learn from the earlier Pasuk.
Why does the Torah see fit to tell us that Yakov left from Be'er-Sheva? If that is where he was living, it is obvious that that is where he left from!
Rashi: To teach us that, when a Tzadik leaves a place, his absence is sorely felt by the inhabitants of the town, 1 for he is the splendor, the beauty and the glory of the town. Consequently, his absence creates a vacuum. 2
Targum Yonasan: To teach us that on the same day 3 that he left Be'er-Sheva he arrived in Charan.
Ohr ha'Chayim, citing the Zohar: The entire Parshah is a hint for man
The same lesson the Torah teaches us in connection with Na'omi and Rus, when they left Mo'av.
Moshav Zekenim: Yitzchak was still there! Having one Tzadik is unlike having two. Tosfos ha'Shalem (21): Also, Yitzchak was blind, and was considered as if he is dead.
The Gematriya of "va'Yelech" equals that of "Bo ba'Yom" (Bereishis Rabah 68:10).
Moshav Zekenim: It is called Be'er Sheva due to the well about which Avraham swore. Ramban - Yakov went to Be'er Sheva to ask permission [from Hashem] to leave Eretz Yisrael, like his father did.
Why does it say "va'Yelech Charanah"? The very next Pasuk records how he stopped before getting there!
Rashi #1, Rashbam and Seforno: The Torah is not telling us that he went straight to Charan, but that he left in order to go to Charan. 1
Rashi #2 (on Pasuk 17): Yakov actually went to Charan. However, when he arrived there, he realized that he had passed Har ha'Moriyah (where his fathers had prayed) without praying there, so he went back there to pray.
Ohr ha'Chayim #1: "Va'Yelech Charanah" teaches that Yakov merely had to leave, and Charan came to greet him (Kefitzas ha'Derech).
Ohr ha'Chayim #2: "Va'Yelech Charanah" teaches that once he left, the Charon (anger) of Esav departed. According to the opinion that Esav sent Elifaz to kill him, these words allude to Elifaz.
Malbim: This is one of four reasons 2 why the Nevu'ah he would receive was through an unclear glass (like all Nevi'im other than Moshe). Since he headed towards a place without Kedushah, this clouded the prophecy, even though he was in Eretz Yisrael.
Riva: He first went to the Yeshivah of Ever, It cannot be that he went straight to Charan, for the Gemara explains that "he encountered the place" refers to Beis-El, which is sill in Eretz Yisrael. Ha'Emek Davar
Why is the break at the beginning of this Parshah closed?
Hadar Zekenim, Da'as Zekenim: It is because Yakov left covertly 1 without telling anyone, due to Esav, like one who flees.
Moshav Zekenim: Normally, people bring money to a Chacham and ask him to marry their daughter. Yakov needed to pursue a wife and work. It was improper for a man like him to work.
Tosfos ha'Shalem (2): The Torah already mentioned at the end of the previous Parshah that Yakov left. This is merely matters written above 2 . This is why Rashi did not ask why it is closed, but he asked about the start of Vayechi. 3
Elsewhere, it says about the Avos "va'Yelach". Why does it say here "va'Yetzei"?
Tosfos ha'Shalem (4): The Avos used to go to dwell elsewhere, and return. Yakov did not intend to return. 1
His mother told him to go only until Esav's anger will subside! Perhaps Yakov did not expect it to subside (PF).
Why is va'Yetzei Yakov put right after Esav marrying Machalas?
Tosfos ha'Shalem (8, citing R. Avigdor): This shows that one may leave Eretz Yisrael only to learn Torah or marry. 1
Tosfos ha'Shalem (22): This teaches that exile atones (brings Mechilah).
How may we learn this? The Torah does not explicitly say that Yakov went to learn. And Yakov himself left in order to marry! And in any case he was permitted to leave due to danger! Perhaps this is why we need to learn from the adjacency. Bava Basra 91a permits to leave amidst very harsh economic conditions. (PF)
Why does it say that he went to Charan? Yitzchak sent him to Padan Aram!
Tosfos ha'Shalem (27): Perhaps after Terach died, Lavan went to take possession of his inheritance in Charan. Yitzchak did not know this.
Midrash Sechel Tov: Padan Aram is close to Charan. 1
Redak (Bereishis 25:20): Padan Aram is a region including Ohr Kasdim, Charan and other cities.
Chizkuni: They are the same! Rivkah told Yakov to go to Charan, and Yitzchak said right after "to Padan Aram" (27:43, 28:2).
Therefore, we need not be concerned if they are used interchangeably. (PF)
Why is the Targum of Be'er Sheva 'Be'era d'Shava'? Everywhere else, Onkelos simply writes Be'er Sheva!
Ha'Emek Davar (from Pesikta Zutresa): Chazal expounded 'from Be'erah of Shevu'ah'