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>that doesn't rule out the possibility that errors or inaccuracies could have been faithfully passed down
Here the issue with that objection. How do we, from a historical standpoint, address that? Certainly many of us could postulate thousands of possibilities of the transition of the biblical books, even within the days of the author's lifetime, but realistically we have to evaluate with evidence we're given and push aside wild assumptions. It's unfruitful otherwise.
>things like the genealogy of Jesus in Matthew
Uhm, the genealogy was an emphasis that Jesus Christ was a descendant of Adam, Abraham, but most of all David the king. You might be wondering why there's a difference between that genealogy from Luke. The gospel according to Luke was focusing Jesus's biography and Luke's Genealogy was from Mary side of the family starting with her husband (in those cultures, the spouses are "adopted" to the others' families).
>the cruelty of God in the OT.
The Hebrews violated their covenant(s), which the equivalent of cheating on a wedding vow. I, like everyone, would become revengeful if that occurred to me, but more importantly God always plea/allow the hebrew to return in His flock if only they'll to repent and return to Him.
>And it has always somewhat bugged me that Jews are seemingly so much more free to question/interpret the Bible/Torah than Christians.
Liberal Jews (AKA. reform jews) think most of the bible is mythology and traditional Jews believe in traditions called the midrash, which make them think that the Pentateuch itself is incomplete, etc. It also doesn't really help that modern Christian are captivated more with emotional arguments than logical ones, so that's why we rarely discuss this topic except in passing.