1)

Why did Yaakov go to Har ha'Gil'ad?

1.

Targum Yonasan: Because he foresaw that Yisrael would require salvation in the days of Yiftach (ha'Gil'adi). (Presumably, he prayed on their behalf - EC.)

2.

It is along the most direct route from Charan to Chevron. (CS)

Sefer: Perek: Pasuk:

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