Judges were individuals called by God to render decisions in cases between the people and to give some leadership. I don’t think we should understand that every judge was over the entire people of Israel. Some of the judges may have had a small area of influence, and many of their periods of judging most likely overlapped. The last judge was Samuel and his time frame was after the other judges and up into the period of the first two kings. The word Negev, often encountered in Scripture simply means “south” or “southern part of the land.”
The section dealing with Caleb is repetitive, but remember that although God is directing the writing of Scripture He allowed the vocabulary and the personality of His writers to come through. They did not know that all the books would someday be put together into one large volume and when they knew something was important, they recorded it.
In just the first chapter we learn that after the death of Joshua the people are not living as they ought to live. In the latter portions of the book of Joshua we read that they did not get rid of all the sinners. Here we read that those sinners are gaining strength and whipping up on those who are supposed to be God’s righteous people. IF they were so, the sinners would not overcome them (per Joshua 23:12-13, 16; see also Judges 2:20-23)!).
2:6-10 sounds too much like America today . . . The great leaders and those who knew God well have died off and the present generation is cocky and ignorant [in SO many senses of the latter word]. This does not mean that there were/are not any good people to serve God, just that the majority did not. The problem then is that just as the few evil amongst a good people receive blessing, so too the few good souls amongst a sinful people are subject to (some of) the punishment (2:11-23; compare Deuteronomy 28).
From 3:1-2 it sounds to me that God not only condones war (against the ungodly), but that He also wants His people to be good at it. What do you think?
Already in chapter 3 (verses 5-8) we see that the people have not learned from their first punishment for sinning against God and are even worse than the previous generations and are being punished yet again (also per Deuteronomy 28 and Leviticus 26).
Continuing the thought from the first portion of Psalm 49 the sons of Korah tell us that no matter how highly folks think of themselves, they will still die and have to face God. BUT I will love and serve Him and He, the only One who can, will redeem me from sin and hell!