What is the connection between the development of Yakov's family discussed here and the development of Esav's family at the end of Vayishlach?
Rashi #2: When Yakov saw all the chiefs that emerged from Esav, he was concerned as to how he would be able to conquer all of them. The answer lies in the following Pasuk "These are the generations of Yakov, Yosef... ", who was the nemesis of Esav. 3
Ramban: To teach us that Esav's descendents moved to a land of their own, whilst Yakov opted to live in a land where his father sojourned but that did not belong to him, in fulfillment of the decree that was issued to Avraham - that they would be "strangers in a land that was not theirs". 4
Rashbam: To teach us that Esav moved away to make way for Yakov, who lived with his father in the land of his fathers, because the law of Bechorah pertained to him.
Oznayim la'Torah #1: As long as Yakov was living in Padan Aram, Esav had the edge over him in two regards - (a) Kibud Av va'Eim and (b) Yishuv Eretz Yisrael. Now that Esav had moved to Har Se'ir, giving up both advantages, Yakov arrived in Kena'an and lived with his father, thereby fulfilling both Mitzvos and reversing the roles in his favor. 5
Oznayim la'Torah #2: The Torah is pointing out why Esav merited having a national heritage and a king, whereas it would be eight generations before Yisrael would be able to do so. This is because, whereas Esav's children, despite the fact that they descended from different mothers, lived in harmony. Thus they were able to appoint a king over the entire tribe. But how could Yisrael, who could not get along with each other, possibly do the same? See how, the moment that one of them insinuated in a dream that he would become king, all the brothers turned against him! 6
In the same way as it did with the ten generations between Adam and No'ach and the ten generations between No'ach and Avraham.
Rashi: This can be compared to a person who is searching for a jewel that he dropped in the sand. He quickly sifts through the sand until he finds the jewel, at which point he throws out the sand and takes the jewel.
Refer to 30:25:1:1. This too, can be compared to a black-smith into whose shop entered a camel laden with flax. When he wondered as to where they would place all that flax, one smart fellow suggested that one spark from his anvil would quickly burn all of it (Rashi).
See also Oznayim la'Torah DH "Vayeishev Yakov", 1, 2.
Oznayim la'Torah: And this will also explain why the Torah begins with the episode of the sale of Yosef.
Why does the Torah say "va'Yeshev Yakov b'Eretz..."?
Rosh: Va'Yeshev is an acronym for the afflictions that befell him, i.e. [the temporary loss of] Yosef, Shimon, and Binyamin.
Moshav Zekenim: His father was Gar there (Megurei Aviv), i.e. amidst fear). Yakov wanted to be Yoshev (settle), tranquilly, unlike the decree Ger Yihyeh Zar'echa (15:13). (It says va'Yeshev also regarding Avraham (13:18) and Yitzchak (25:11), and Chazal did not expound so about them! - PF)
When Tzadikim seek tranquility, Hashem reminds them that their reward is reserved for them in Olam ha'Ba and that they should not be looking for it in this world as well (Rashi). Hashem says, My Simchah (Chanukas ha'Mishkan) did not last long [before Nadav and Avihu died] - do you want extended Simchah?! (Hadar Zekenim from Midrash Tanchuma).
Why must it say both "b'Eretz Megurei Aviv" and "b'Eretz Kena'an"?
Riva, Moshav Zekenim: B'Eretz Megurei Aviv could refer to Avraham [who initially lived in Aram; grandsons are like sons]. Had it said only b'Eretz Kena'an, we would not know in which city.
Ohr ha'Chayim: Even though Esav took his inheritance, and even though Hashem promised the land to Yakov, he lived in it like a stranger, and treated it like Eretz Kena'an (not his own land).
Ha'Emek Davar: It explains why Yakov was particular to live here, even though the Brachah of [receiving] the land would not apply to until after exile. His fathers already implanted Kedushah in the land, and there is a Mitzvah of dwelling in Eretz Kena'an, and it is most conducive to Taharas ha'Kodesh.
Why must the Torah say that he lived "b'Eretz Megurei Aviv b'Eretz Kena'an"? It already said that he went to Chevron, and did not say that he left!
Refer to 37:1:151:2,3.
Malbim: The Torah explains that without special Hashgachah, Yakov would never have gone to Egypt (e.g. due to famine), for it was his fathers' land, and Eretz Kena'an is conducive to Kedushah.
QUESTIONS ON RASHI
Rashi writes that Yakov intended to settle down tranquilly. Why did he want this specifically now?
Oznayim la'Torah: Because until now, many troubles had befallen him, either because he had failed to fulfill the vow that he made on his journey to Charan or because of his failure to fulfill the Mitzvah of Kibud Av (and Yishuv Eretz Yisrael). Now however, that he made up for these deficiencies, he thought that it would be in order to settle down.
Rashi writes that Yakov intended to settle down tranquilly, therefore the incident with Yosef was sprung upon him. What is the direct connection between them?
Oznayim la'Torah 1 : As long as the Avos sojourned in the land, 2 their years of Geirus were included in the 400 years of Galus decreed upon Avraham's children. 3 The moment however, that Yakov decided to settle in the land, the time had come to go down to Egypt and suffer slavery 4 (Galus Mitzrayim). The sale of Yosef served as the prelude to Galus Mitzrayim as well as ensuring that Yakov would go down to Egypt honorably, and not in chains.
Rashi writes that Yakov intended to settle down tranquilly - Hashem said, is it not enough for them that their reward is reserved for them in Olam ha'Ba...?! Why is it sinful to live tranquilly in this world?
Oznayim la'Torah (citing his son, R. Elchanan): It is not sinful to live tranquilly in this world. 1 What is sinful is for Tzadikim to request to live tranquilly in this world - because by so doing, one attaches undue importance to this passing world.
Oznayim la'Torah: Indeed, the Gemara in a number of places talks about inheriting this world and the next - See for example, Berachos, 16b.