The Lord was with the men of Judah. They took possession of the hill country, but they were unable to drive the people from the plains, because they had chariots fitted with iron. Judges 1:19
What does this do to our thinking about God and his ways?
Why do you suppose that God didn't just magically poof away the "enemies" in the Promised Land?
Does God do anything outside of communal agreement? What I mean is, certainly we don't think, "God wanted to clear out the hill country but the iron chariots were a little too difficult for our world making God so the Almighty was unable to drive them out."
Instead, it apears to me that this entire chapter is about how after the time of Joshua (or around his death) we can start to see the ways that human agreement/disagreement with God changes things--sometimes the tasks are too great in the minds of the humans so God doesn't force it. (V19)
Perhaps, in other places when the humans are succesfull, this generation seems to be wanting more than they should expecting--(at least that seems one way to look at the Othaniel stuff in this chapter.)
In much of the chapter, this seems to me to be the point. God wanted the people to unite with him in his plan, but he left room for them to say things like (not now, too old, they're too tough, too determined, let's compromise the plan, yadda, yadda)
It's a terrifying frustrating turn of events.
Several times in our reading we are told that God was with them, but...
The Lord was with them...but they left these guys alive
The Lord was with them...but they took more than they should
The Lord was with them...but they adjusted the plan
By the end of the reading we get this as the foreshadowwing of what the book od Judges has in store for us...
Whenever Israel went out to fight, the hand of the Lord was against them to defeat them, just as he had sworn to them. They were in great distress.
16 Then the Lord raised up judges... Judges 2:15-16
Here we go...keep reading.