What are the implications of "Vi'yeshavtem ba'Aretz"?
Rashi: It implies 'after the distribution of the land, when each person knows where his portion is and the tribal territories have been clarified. 1
Torah Temimah: Refer to 17:14:1:1.
With occurred fourteen years after they entered the land.
Which time-period is "Ve'he'niach lachem mi'Kol Oyveichem" referring to?
Rashi: It hints at the era of David ha'Melech. 1
Rashi: When they finally attained respite ("ve'Heni'ach") - Menuchah) from the nations that Hashem'" (Shoftim, 3:1). Rashi (on Pasuk 11) and Targum Yonasan: That is when the obligation to build the Beis-Hamikdash in Yerushalayim will come into effect (as the next Pasuk teaches us), See also Shmuel 2, 7:1.
What are the connotations of the words "Vi'yeshavtem Betach"?
Rashi: It means that, after they have respite from all their enemies and dwell in security, they should build the Beis-Hamikash - (to teach us that, of the three Mitzvos that will come into effect after they enter the land, 1 destroying Amalek takes precedence over buiding the Beis-Hamikdash - (Sanhedrin, 20b). 2
Targum Yonasan: It means that, after they enjoy respite from all their enemies and build the Beis-Hamikdash, they will dwell in safety.
Refer to 12:11:0.1:2 See Torah Temimah, citing Sanhedrin, Ibid. and note 34.
And so does appointing a king. See Torah Temimah, note 35.