Why did Moshe repeat his request for Hashem to accompany Yisrael?
Oznayim la'Torah: Based on the following Pasuk, it seems that he was asking Hashem to enter into a covenant with Yisrael in this regard 1 - and Hashem acquiesced to this request as well.
To cover them in the event that they sinned again (Oznayim la'Torah).
Why did Moshe's request for Hashem to accompany Yisrael depend on the fact that they were a stubborn nation?
Rashi and Rashbam: With reference to the thirteen Midos, Moshe was saying that, Hashem could safely travel with them, because, even 'if', 1 in their stubbornness, they rebelled, and in spite of what He said earlier 2 "Pen Achelcha ba'Darech", He would forgive them, seeing as He carried sin (as He had just informed him).
Ramban, Targum Onkelos, Targum Yonasan and Hadar Zekenim #1: It is precisely because Yisrael are prone to sin that they need Hashem (who had just forgiven them), to go with them. 3 Moreover, Hashem is interested in their well-being, seeing as they are His people and His inheritance (as the Pasuk goes on to explain).
Seforno and Hadar Zekenim #2: In spite of Yisrael being stiff-necked - and therefore bound to sin, it is preferable that You go with them (even though the sin of the people will be much bigger) 4 than a Mal'ach, because, whereas a Mal'ach does not have a mandate to forgive, 5 Hashem will forgive them. 6
Toras Avigdor (Vayera p.9): Because they are stubborn, Hashem should accompany them - because, in their stubbornness, theyignore all the follies of the world.
Oznayimla'Torah: It is precisely because they are stubborn that they need Hashem to go with them - to teach them to go in His ways, because, once they are trained to do so, they will hold on to them tenaciously and never deviate from them. 7
Rashi: Here, "Ki" means 'if', and not 'because'.
See 33:16 (Rashi).
And not a Mal'ach (who is not able to forgive - Ramban). In contrast to earlier, when Hashem was angry with them, and He would have destroyed them had they sinned (See 33:3), in which case it would have been preferable to have sent a Mal'ach, as the Torah wrote there (Ramban).
As Hashem Himself pointed out earlier. See 33:5 (Seforno).
As the Pasuk stated in 23:21 (Seforno).
As He said He would in the thirteen Midos.
See Oznayim la'Torah, who elaborates.
What are the connotations of "u'Nechaltanu"?
Rashi and Ramban: It means that Yisrael, exclusively should become Hashem's inheritance. 1
Targum Yonasan, Da'as Zekenim and Hadar Zekenim: It means that He will enable Yisrael to inherit the land that He promised to their fathers (and that he will never exchange them for another nation - Targum Yonasan).
