1)

Why does it say that the donkeys were lost to Kish?

1.

Malbim: They were not truly lost, just they were hidden at the time due to Kish, in order that Sha'ul would go to seek them.

2)

Why did he ask his son to seek them, and not his servants?

1.

Malbim: Hashem put this in his heart.

Sefer: Perek: Pasuk:

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