1)

Why did he say "Mi Yovileni Ir Mivtzar"?

1.

Rashi: Who will take me in the days of Mashi'ach to conquer Esav's fortified cities?

2.

Malbim (60:11): How did I conquer Batzrah, if You did not help me?! This shows that Hashem did not abandon them also at the beginning. He let the enemy conquer Shechem and Emek Sukos for Yisrael's benefit, so that Mo'av, Edom and Peleshes would fall to them.

2)

What is the meaning of "Mi Nachani Ad Edom"?

1.

Rashi: [The One who will take me in Yemos ha'Mashi'ach to conquer Esav's fortified cities is] the One who led me over (to conquer) fortified cities of Edom - I struck 18,000 of them in Gei Melach.

2.

Malbim (60:11): Who led me to Edom? Naturally, I could not get there; it was only via Hashem's help!

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