1)

What is "ba'Derech Asher Tishlachem"?

1.

Radak: This is like "va'Yhi Devar Shmuel l'Chol Yisrael" (Shmuel I, 4:1), and when they asked from the Urim v'Tumim, like in the war against Binyamin (Shoftim 20:18, 23), and similarly when there will not be a punishment on them.

2.

Malbim: When they merit, they will go to fight the enemy outside Yerushalayim, in Eretz Yisrael.

2)

What is praying "Derech ha'Ir"?

1.

Rashi: They face Yerushalayim.

Sefer: Perek: Pasuk:

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