Jephthah may not have been a model of discernment (he didn't have to sacrifice his daughter like he swore to, even under the law; cf. Lev. 5:4-6), but his dialogue with the king of Ammon provides some additional detail re: the last leg of Israel's wilderness journey. For example, Moses' appeal to Moab (11:17) is not mentioned in Num. 20, where the appeal to Edom is (vv. 14-21) or Deut. 2, where God tells Israel not to meddle with Edom, Moab, or Ammon (vv. 5-19), on account of their kinship with Israel. What I found most interesting in Judg. 11 was v. 20, where we learn that the underlying reason for Sihon, king of Heshbon, attacking Israel was not trusting them to pass through his land pacifically, like they promised (Num. 21:21-23). Sihon's mistrust here was a fatal mistake, since Israel would've bypassed him with the intent of crossing the Jordan north of him to enter Canaan.
On a practical note, trust is a matter of discernment (didn't Joshua learn that later with the Hivites?! cf. Josh. 9). Sometimes you should trust, and sometimes you shouldn't. But trust you must at some point, since "He who trusts no one is not to be trusted" (proverb). Only God deserves our absolute trust (Ps. 62:8), but you will have to trust others to some degree to "live peaceably with all men" (Rom. 12:18). Even if you must trust others, God is in control of the outcome, so rest in his care.
Bro. Jared
1 Thes. 2:4, 2 Tim. 2:2 (God-->apostles-->faithful men)