The "timeline" idea was implemented in a series by EWTN's Jeff Cavens. You can find lots of products related to using this bible study method at the ewtn.com website, look into the catalogue tab, probably under "books" or "bible study"
The Pontifical Biblical Commission issued a document around 1992 that recommended reading the Bible alongside a commentary. But, they did not elaborate further on recommending a commentary.
The PBC elsewhere also endorsed reading Jewish commentaries for the part of the Bible we call the Old Testament, calling them first class bible study aids -- with the caution that they have a different point of view than do Catholic Christians.
The Torah series of commentaries from the Jewish Publication Society are very detailed. They're fairly expensive, to be sure. They take a good look at the Hebrew words of the text in great detail, to give the English reader a good understanding of the words. There's more questions about translation in the Jewish commentaries than you may expect. The JPS commentaries have no index to them, so you have to maintain your own.
The NJPS (New JPS translation of the Hebrew Bible) translates Deut 12:18 to have the word "happy" in it. Jews accept that they are commanded by God to be happy. My Revised Standard Version - 2nd Catholic Edition translates the word there as "rejoice." It takes a lot of reading (if not dedication and luck) to pick up on subtleties like this.
I'm currently reading Deuteronomy ("Devarim") in The Jewish Study Bible from Oxford U. Press. The commentary points out changes in "the law" (if you want to call it that).
The hypothesis that Moses wrote all the books of the Torah (first 5 books of the Bible) is challenged by several changes that occur between Deuteronomy and earlier books. One, the passover meal of the lamb in one place says that it's supposed to be roasted; in Deut., another method of preparation is specified -- boiling. You might not expect this difference from the same author. the study bible suggests that the instructions in Deut come from a different tradition than that in Ex and Lev.
Another difference is the Ten Commandments in Ex versus Deut. In one place it says to "observe" the Sabbath, in the other it says to "remember" it. Those are different. Why?
In Ex and Lev,the temple priests are descendants of Aaron, and the Levites are just temple workers. In Deut, the Levites are priests offering the sacrifices. No explanation of the change -- except to bolster the "documentary hypothesis" there were many authors of the Torah, with different traditions, and evolving practices.
In the earlier books, it's very clear that the Levites serve at the temple and do not hold any territory in the Promised Land. But, guess what? In Deut, the Levites ARE assigned a holding of land. The commentary says that perhaps the earlier scheme simply didn't work, and the Levites were given an assignment of land after the return from the Babylonian captivity.
Without a detailed commentary, simply reading the Bible cover to cover, you would certainly miss such details. Do you care about this?
The Cavens Timeline program may be the best starting place, but I'd suggest not stopping there.
continued in my next post.