One of the best ways to understand Scripture in all its fullness is to get into the life setting and culture of the time period. Trying to read into Scripture 21st century concepts will never work.
My children enjoy watching "Leave it to Beaver." When they first started watching they thought it was so funny because of many of the sayings on the show from the 50's. One of the "weirdest" ones to them was "he's giving you the business." I actually had never heard of that one myself until hearing it on the show. We don't say "he's giving you the business" anymore, and unless you go back even to the 1950's to understand what that phrase means, you won't get the most out of the show. I'll let you do the research on that one yourself. ;)
One of my favorite passages to go to when talking to people about understanding the culture of the ancient Hebrews is Deuteronomy 22:5. There are entire organizations or denominations who will quote this verse and declare that it is an abomination for a woman to put on a pair of pants. This is because as they grew up in the 1900's in America, pants were considered to be the garment of men. They then take a 20th century mindset and force it into a text that was written thousands of years ago. What they should have done is go back to the culture and life setting, when the commandment was first uttered. Just a little bit of study shows that both men and women wore the same basic apparel, robes or tunics. Yahweh was not telling the man to not put on a skirt, nor was he telling the woman not to wear pants. Something entirely different was being commanded, but of course you'd never know that if not studying the culture.
Many more examples could be given, but what I'd like to do is share a few resources that have been helpful to me in studying Hebrew culture. Hopefully these will aid you in your studies as well.
1. New Light on the Difficult Words of Jesus (by David Bivin)
Mr. Bivin deals heavily with the sayings during the time of Yeshua. This book helped me understand what Yeshua was actually saying when he said he didn't come to destroy the law but to fulfill it. I discovered that Matthew 5:17 was even abused to some extent by pro-Torah teachers.
2. Yeshua: A Guide to the Real Jesus and the Original Church (by Dr. Ron Moseley)
Dr. Moseley covers so many Hebrew idioms in the teaching of Yeshua in chapter 2, and he also points out that we must recognize that there was more than one group of Pharisees in Yeshua's day. There were actually seven groups! Much more is covered as well.
3. The Life and Times of Jesus the Messiah (by Alfred Edersheim)
Mr. Edersheim lived in the 1800's and was born to Jewish parents before converting to the Presbyterian branch of Christianity. Mr. Edersheim has done much of the "leg work" when it comes to understanding the life setting of Yeshua's day. This volume is priceless as it is over 1,000 pages in length.
4. The Temple: Its Ministry and Services (by Alfred Edersheim)
Another excellent work by Edersheim, focusing in on what took place at the Temple in Jerusalem. Covers all of the festivals (including the Sabbath and New Moon), and the order and meaning of the sacrifices. From this book I learned what Yeshua really meant when he said in Matthew 6 not to sound a trumpet when you give alms.
5. Commentary on the NT from the Talmud and Hebraica (by John Lighfoot)
Bishop Lightfoot lived in the 1600's and studied extensively into the traditions of the elders that we call the Talmud. Understanding this helps greatly in understanding Yeshua's controversies with the Pharisees, Sadducees, and scribes of his day.
6. Manners and Customs in the Bible (by Victor H. Matthews)
Geography, Burial Customs, Food, Weapons, and so much more is covered in this work by Mr. Matthews. This is another invaluable source when trying to get "into the mind" of ancient Hebrews.
7. And of course you have the Works of Philo and the Works of Josephus, two men which lived right around the time of the Messiah. One cannot really say enough about these two historians and their works. They are a must have for the library of the serious student of Scripture.
I'm certain there are other books in my library that I've learned Biblical culture from, but these are the ones I go to the most in my studies.
Blog by Matthew Janzen. Lover of Yahweh, Yeshua, my wife and 5 children. All else is commentary.