Why did Yaakov bury Rachel on the way? Why did he not bury her in Me'aras ha'Machpelah, or at least in nearby Efrat?
Rashi and Rashbam: Refer to 35:16:1:1*.
Rashi (to 48:7, based on Bereishis Rabah 82:10): He did so by Divine decree, 1 so that when Bnei Yisrael would pass her grave as they were being led to Bavel into exile, she would weep 2 and beseech Hashem for mercy on their behalf. 3
Ramban (to 35:16): Because he wanted to bury her in the territory of her son Binyamin, and he foresaw that Efrat would be given to Yehudah. Malbim - this is why the Torah says "Hi Beis Lechem" (which we know is in Yehudah). She was buried on the road, in Binyamin's portion.
Targum Yonasan and Ramban (to 48:7) #1: Because, under the difficult circumstances, 4 he was unable to transport her. 5
Ramban (to 48:7), from Moed Katan 27a: It is forbidden to delay the burial of a woman (even for a short while due to Kavod ha'Mes, lest she exude blood). 6
Ramban (to 48:7) #2: The real reason that he declined to bury Rachel in the Me'aras ha'Machpelah was in order not to bury two sisters in the same grave, so as not to be embarrassed before his fathers. 7
Moshav Zekenim #1: He did not want to live in the city. (If he would bury her there and leave,) even if he bought the place around it, they would steal it and plow it.
Rosh, Moshav Zekenim #2: It was in Chutz la'Aretz, 8 and in any case she would not stay there (Mesim come to Eretz Yisrael through tunnels).
Chazal say that Ru'ach ha'Kodesh/ prophecy dwell only amidst Simchah. Was Yaakov b'Simchah after she died?! Perhaps indeed, he was (refer to 35:21:151:1)! Or perhaps Hashem told him just before she died. (PF)
Rashi: As the Navi Yirmeyahu (31:14) tells us. Hashem did indeed hear her weeping, and promised her, "the children will return to their borders" (Yirmeyahu 31:16).This is what Yaakov himself informed Yosef, to allay Yosef's grievances at his having done so (Rashi). And this is hinted in the word "ba'Derech" here (Ramban to 48:7).
Moshav Zekenim: She has great power of Tefilah. She bore the pain of a rival who entered her house, lest Leah be shamed, so she can ask Hashem to bear a rival (idolatry) brought into His house. (Perhaps the text of the Rosh should say so, just there is a printing mistake - PF.)
Bearing in mind that he was traveling with his entire family and all his belongings (Ramban). (He could have left his possessions with his servants! Perhaps he feared to leave them alone, lest they graze the animals in others' property. Or, he could not travel quickly with a newborn baby, and he would not entrust them with Binyamin - PF.)
The Ramban here is actually presenting Yaakov's answer to Yosef, to explain why he did not bury her in the Me'aras ha'Machpelah, which was merely a half-day journey from where she was actually buried.
Refer to 48:7:2:2. Ha'amek Davar citing Moed Katan 28a - some say that this is only for one who died amidst birth (she is very prone to exude blood). This was Hashem's way to cause that she be buried on the road (refer to 35:19:1:2).
Ramban: And Leah was the one that he married first (b'Heter).
Hagahah (in the Rosh): She was buried in Eretz Yisrael! Perhaps he means that she died just outside Eretz Yisrael, like the Ramban (26:5), who says that the Avos kept all the Mitzvos (including the Isur to marry two sisters) in Eretz Yisrael.
Why did Rachel die so young?
Rashi (to 31:32): Because Yaakov unwittingly cursed her when he declared to Lavan, "the one with whom you will find your gods, he will not live" (31:32).
Why does it say that she died? The previous verse says so!
Ha'amek Davar: During a difficult birth, it often looks like the mother died, but really, she merely fainted amidst weakness. They tried reviving her, but she died (Zohar).