There is some some controversy as where to start this section since verses 13:32-33 act as a swing passage both summarizing the preceding land distributions and introducing the next major section which ends at 14:5 dealing with the position of the Levites. We can recognize that division by the way it is bounded at both ends with similar statements:
“But to the tribe of Levi Moses gave no inheritance” (13:33)
“But to the Levites he gave no inheritance among them” (14:3)
“No portion was given the Levites in the land” (14:4)
The next major literary unit is similarly bracketed by another repeated phrase:
“Caleb son of Jephunneh the Kenizzite” (14:6)
“Caleb son of Jephunneh” (14:13)
“Caleb son of Jephunneh the Kenezzite” (14:14)
Note the literary similarity between these two sections in that the concluding phrases in each are repeated in adjacent verses. I should also point out that the final statement “And the land had rest from war” also concluded an earlier section in the book at 11:21-23.
The following more specific comments from the literature lean heavily on several anonymous articles in The Dictionary of Biblical Imagery.
Joshua 14:2 Howard says, “The land is seen as God's gift to Israel over and over again, especially in Deuteronomy. In Joshua, the concept appears over fifty times. As a gift of God, it never belongs absolutely to Israel: it belongs to God...The dividing of the land by lot further indicates that it was at God's disposal (Num. 26:55-56; Josh. 14:2; 18:1-10)...”
Younger notes that, “Ironically, it was the fear of these very Anakim that caused Israel's disobedience and failure at Kadesh-barnea according to Num. 13:28 and Deuteronomy 1.28.”
Joshua 14:3-4 Woudstra: “Starting from the basic figure of the twelve-tribe arrangement, these verses explain the relationship between the 2-1/2 tribes east of the Jordan and the 9-1/2 west of the river. Apparently it was necessary to make even more clear that which was obvious from the preceding chapter (13:7-8). Special concern is shown to emphasize that the tribes on the east side of the Jordan indeed did belong to Israel.”
Joshua 14:7 Gray explains that “forty is the conventional indefinite number in Semitic folklore. It indicates a man in his prime...Caleb's age at this point is given as eighty-five (v. 10).”
Joshua 14:8 “The image of melting is most commonly used in the Bible to describe the effects of fear...The result of this breakdown is often terror: 'our hearts melted and no courage remained in any man' (Josh 2:11 NASB; cf. Josh 5:1; 7:5; 14:8...).” (DBI)
Joshua 14:9 DBI: “Ideally, parents...provide a homeland (Josh 14:9; Jer 30:20; Acts 7:5). It is their great sense of responsibility that prompts their continued quest for the Promised Land.” One might easily extend that principle today in order to state that it is a parent's grave responsibility to prepare their children for their eventual Heavenly Home.
“In ancient Near Eastern iconography we find images of enemies under a footstool, beneath the feet of the reigning king...This image seems to carry the connotation of shaming the enemy (to direct the soles of the foot toward someone was a shaming action) and treading on them in a manner that lays claim to them, perhaps analogous to walking over their territory (Josh 1:3; 14:9; Ps 8:6).” (DBI)
Joshua 14:10 See comment on v. 7.
Joshua 14:11 “Several biblical characters are exceptions to these transformations [accompanying old age] and become powerful images:...Moses and Caleb, who remain strong in old age (Deut 34:7; Josh 14:11). But these are exceptions, and the biblical norm is that one's later years are marked by decline.” (DBI)
Another author in that same source states that “the basic rhythm of life is encapsulated in a biblical merism (the rhetorical device of naming opposites with the implication that everything between them is also included) that speaks of 'going out' and 'coming in' (Josh 14:11, etc).”
Joshua 14:12-13 Butler says, “The Anakim are connected to the primeval wicked giants, the Nephilim (Num 13:33; cf. Gen 6:4...). They are particularly tied to Hebron (Num 13:22,28). Here is another step on the way to fulfillment of the divine promise to destroy these enemies (Deut 9:2...). For Caleb that destruction depends only on the divine promise...The blessing [in v. 13] represents a promise for steady continued success over a long period of time, not just in one particular moment or event...In this case the blessing is for the work of Caleb and his descendants in Hebron.” As Paul puts it in Romans 8:31, “If God is with us, who is against us.”
Joshua 14:14 “Also ironically [see comment on v. 2 above], this prime example of Judahite success is accomplished by a non-Israelite: Caleb is a Kenizzite (14:14) who is, however, ultimately incorporated into Judah's genealogy (1 Chr 2:9,18).” (Younger)
Joshua 14:15 “The idea of rest for the entire nation from their enemies is found in such passages as Deuteronomy 12:10 and 25:19, and it is echoed in summarizing passages in Joshua 21:44 and 23:1. In two places, we read that the land itself had rest from war (11:23; 14:15; cf. Deut 12:9-10; 25:19; 2 Sam. 7:1,11; 1 Kings 8:56). That anticipates the same idea repeated several times in Judges: 'And the land had rest____years” (3:11; 3:30; 5:31; 8:28).” (Howard)