Why did Hashem inform Yisrael that a Mal'ach would bring them to Eretz Yisrael and not He Himself?
Da'as Zekenim #1, Hadar Zekenim #1: In the merit of Aseres ha'Dibros, which begin with Anochi, Hashem said Anochi (I) will send an angel to guard you.
Da'as Zekenim #2, Hadar Zekenim #2: Hashem will send the hornet [to help us conquer Eretz Yisrael]. In the future, he will send Eliyahu ha'Navi.
Moshav Zekenim: The Shechinah accompanied Yisrael, and also Sar ha'Panim (Hashem's primary angel) - "u'Mal'ach Panav Hoshi'am" (Yeshayah 63:9), "va'Yotzi'acha b'Fanav" (Devarim 4:37), "va'Yishlach Mal'ach va'Yotzi'enu mi'Egypt" (Bamidbar 20:16). Even though we say in the Hagadah that Hashem Himself took us out, He was there telling the angel what to do.
Rosh: Mal'ach refers to a Navi (Moshe), like "Mal'ivim be'Mal'achei Elokim" in Divrei ha'Yamim 2:36:16.
See Shemos 33:3 and Sifsei Chachamim. Moshav Zekenim rejects this, Moshe's prayer negated the decree! Ramban (citing the Tanchuma) defends Rashi; the angel returned after Moshe's death, in the time of Yehoshua (Yehoshua 5:13). Moshav Zekenim - this was to inform him that from now and onwards, an angel will be sent in front of them. "Atah Basi" - I was sent in the days of Moshe, and rejected; Moshe did not want me to go with him. Refer also to 23:21:3:3*.
If Hashem was referring to the angel that He would send after the sin of the Golden Calf, why did Yisrael not become dejected and why did Moshe not object as they did when it occurred (See Ki Sisa, 33:3 & Rashi Ki Sisa, 33:12)?
Oznayim la'Torah: Because whereas in Ki Sisa, the Torah is talking about after the sin of the Golden Calf, where Yisrael and Moshe were worried that hey would sin and the Mal'ach would not forgive them, as Hashem had warned them, the current Parshah is talking about the period following Matan Torah, where even Hashem atterted that they had reached the highest levels, 1 they were certain that they would not sin, and there was no reason to be concerned.
Oznayim la'Torah: See Tehilim, 82: 6.
What are the connotations of the words "El ha'Makom asher Hachinosi"?
Rashi #1, Ramban, Targum Onkelos and Targum Yonasan: It means to the location 1 that Hashem designated.
Rashi #2: It is one of the Pesukim which teaches us that the Beis-Hamikdash in Heaven is located exactly opposite the Beis-Hamikdash on earth. 2
Of His Shechinah (Targum Yonasan), with reference to the Beis-Hamikdash, as the Pasuk indicates in Beshalach, 15:17 (Ramban).
Oznayim la'Torah: And a Mal'ach did indeed show Gad ha'Navi the exact location - the barn of Arnon on the Har Hamoriyah, where the Beis-Hamikdash shel Matah was to be built. Moreover, if the Mal'ach was Micha'el, as some commentaries explain, it was most appropriate, since Micha'el is the Kohen Gadol who sacrifices the Neshamos of Tzadikim on the Mizbe'ach shel Ma'alah.