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In short, to understand the Torah, one must apply due diligence in getting inside the heads of the original writers and readers. Getting a real handle on what was said involves lots of cross-cultural study involving history, culture, and literature.
An additional caveat: the Torah cannot be "understood" without application. No one will ever be able to explain the value of the instructions until they have lived them out to some significant degree. There are many who will mock some of the instructions in the Torah. But that's because they have not gone through the exercise. This is what Hebrews 5:14 means when it says, "But solid food belongs to those who are of full age, those who
by reason of use have their senses exercised to discern both good and evil." It is the practice of good that trains us to understand and value that which is good.
Learning the Bible is not so much a classroom pursuit as it is a life pursuit.
I also encourage you to get a good atlas, with maps of Israel and the surrounding countries. You can also find some good references that provide historical and geographical background on each of the books in the bible. In order to learn the culture, I recommend a book like,
The New Manners and Customs of the Bible by James Freeman. That one served me well back in the early 1990's.
Most of all... have fun! Enjoy what you learn, appreciate the nuances, and rejoice as you build your relationship with the Master. If you aren't having fun when you learn, then you're not doing it right <snip>