And Caleb, etc. - See this whole account, which is placed here by way of recapitulation, in Joshua 15:13-19 (note), and the explanatory notes there.

And Caleb. The whole of this account is found in Jos.

Judges 15:13-19 And they spoke to him, saying, No; but we will bind you fast, and deliver you into their hand: but surely we will not kill you...

, and seems to be inserted here by way of recapitulation.

Joshua 15:16,17 And Caleb said, He that smites Kirjathsepher, and takes it, to him will I give Achsah my daughter to wife...

1 Samuel 17:25 And the men of Israel said, Have you seen this man that is come up? surely to defy Israel is he come up: and it shall be...

1 Samuel 18:23 And Saul's servants spoke those words in the ears of David. And David said, Seems it to you a light thing to be a king's son in law...

to him. In ancient times fathers assumed an absolute right over their children, especially in disposing of them in marriage; and it was customary for a king or great man to promise his daughter in marriage to him who should take a city.

Tsippor
"Tsippor is the greatest city of Galilee, and built in a very strong place." "Kitron (Judg 1:29,30) is Tsippor: and why is it called Tsippor? Because it is seated upon a mountain as Tsippor, a bird." "Sixteen miles on all sides from Tsippor was a land flowing with milk and honey." This city is noted in Josephus for its warlike affairs; but most noted in the Talmudists for the university fixed there, and for the learning, which Rabbi Judah the Holy brought hither, as we have said before. He sat in …
John Lightfoot—From the Talmud and Hebraica

Judges
For the understanding of the early history and religion of Israel, the book of Judges, which covers the period from the death of Joshua to the beginning of the struggle with the Philistines, is of inestimable importance; and it is very fortunate that the elements contributed by the later editors are so easily separated from the ancient stories whose moral they seek to point. That moral is most elaborately stated in ii. 6-iii. 6, which is a sort of programme or preface to iii. 7-xvi. 31, which constitutes …
John Edgar McFadyen—Introduction to the Old Testament