1)
When will Hashem appoint the shepherds?
1.
Malbim: In Bayis Sheni. They were not kings, only shepherds.
2)
Why does it say both "Lo Yir'u" and "v'Lo Yechatu"?
1.
Malbim: Yechatu is a smaller level of fear than Yir'u. (They will not have even this small level.)
3)
What is the meaning of "Lo Yifkedu"?
1.
Rashi: They will not lack. This is like "v'Lo Nifkad Mimenu Ish" (Bamidbar 31:49).
2.
Malbim: You did not prevent loss of them via evil beasts. I.e. through you, they were divided into factions, and afterwards went to exile and were killed in wars.