1)

Tzar'ah and Eshta'ol are in Yehudah (15:33)!

1.

Rashi: Dan's portion was nearby. 1 Malbim


1

Yehudah was in the south, and Dan was in the north, like it says "Kol Yisrael mi'Dan v'Ad Be'er Sheva" (Shmuel 1 3:20 and elsewhere). Rashi (Devarim 33:22) says that initially, Dan received in the northwest, and later conquered also in the northeast! Perhaps he means northwest of Yehudah (refer to 19:41:1:2). Also, Shimshon was between these cities (Shoftim 13:25) when Ru'ach Hashem was aroused in him [to confront the Pelishtim]. Eretz Pelishtim was near Egypt (Shemos 13:17, Yehoshua 13:3), southeast of Eretz Yisrael. Did Eretz Pelishtim extend until to the north of Eretz Yisrael?! (PF)

2

The prefix Vov in 'v'Nachalas' means or (or the text should say 'Oh'). Metzudas David gives two answers; each suffices by itself. (PF)

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