You know what you did, when you consolidated the main point of your question in the TL;DR ?
A quick summary of the Bible is what you need to help you get an overview of what is going on!
IF you are not familiar with th e main events & characters in the Bible,
I strongly suggest that you start with:
"My Book of Bible Stories"
http://www.watchtower.org/e/my/section_00.htm
This book puts them in chronological order,
and provides link-references to all of the Bible verses used, story by story.
This is to encourage you to look up & read all of them, along with the story text.
Perhaps the MAIN importance of the Hebrew Scriptures (O.T.) is that they contain many, MANY prophesies about the Messiah, from hundreds of years in advance---which only Christ has fulfilled, thus proving his true identity:
"How Daniel's Prophecy Foretells the Messiah's Arrival"
http://www.watchtower.org/e/bh/appendix_02.htm
"Jesus Christ---The Promised Messiah"
- Prophecies Regarding the Messiah
http://www.watchtower.org/e/bh/appendix_03.htm
The Bible book of Daniel contains some other very important prophecies, too, which are undergoing fulfillment right now. The best introduction to Daniel's prophecies --besides the book of Daniel itself-- is:
"Pay Attention to Daniel's Prophecy!"
http://www.watchtower.org/e/publications/index.htm
It aids the reader to examine the entire book of Daniel, verse by verse, comparing them to relevant verses elsewhere in the Bible, as well as to world history. (I found it very exciting reading, as it shows how other prophesies & things tie in!)
Instead of trying to read the Bible straight through, without knowing anything about what you are reading, I found it much more rewarding to glean the main teachings first, and then going back & piecing them together. I do suggest starting with the prophecies regarding Christ --then & now & future-- though, because that is of the highest relevance for our day!
You can quickly find where the Bible speaks of different main issues, by researching it with the help of the Bible study aid:
"What Does the Bible Really Teach?"
http://www.watchtower.org/e/bh/article_00.htm
Another thing that you may want to look into, is locating a Bible that is much more up to date than the KJV, as well as in modern English . . . The more modern translations have much older & more accurate sources than the KJV did in 1600!
"How You Can Choose a Good Bible Translation"
- From One Extreme to the Other
- Are Word-for-Word Translations Best?
- What About Free Translations?
- Why the Need for Caution?
- Finding the Best Translation
http://watchtower.org/e/20080501a/article_01.htm
When you are starting out, the main thing to look for is what it indicates about our Creator, and mankind's relationship with him. Students of the Bible never stop learning new things each time they re-read it. Each reading works as a laying of a foundation, for building upon during the following reading!
Here are 3 more articles that may help encourage you:
"Can the Bible Be Understood?"
- How You Can Understand the Bible!
http://watchtower.org/e/20090701/article_01.htm
"Do You Allow God to Speak to You Every Day?"
http://watchtower.org/e/20090801a/article_01.htm
"What Is the Value of the 'Old Testament'?" :
- Is the 'Old Testament' Still Relevant? [Yes!]
- It Was 'Written for Our Instruction'
http://watchtower.org/e/20070901/article_01.htm
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