I think if we really want to get a deeper look at the Old Testament from the [Language] it was written in. The Jews explaining the Tanakh is a valuable choice to make. To ask their views on Yeshua and the New Covenant, is good for conversation. For me, the Old Testament is Jesus Christ. Every time God was in [person form] dealing with Abraham, Joshua, Moses,' Jacob, Adam/Eve and so forth it "was/is" the WORD. Even as a Burning Bush calling Himself Elohim and I AM to Moses, He was/is the WORD. Even though the Jews do not look at the WORD here in the Old Testament as Yeshua/Jesus, they still can explain what is happening in the Hebrew Language from passed down word of mouth tradition. We can then apply that as it was the WORD who would eventually be made flesh as our Sacrifice and being the God who also dealt with humanity in the Old Testament. The Bible as a true [lineage] account also is the Story of the WORD from Creation to End.
If you do you should be ready because many Christians end up in Jewish roots,COG,WWCOG ect. and instead of "converting Jews" they end up "converted themselves". The Jews for the most part believe the New Covenant only applies to them and so to them it has nothing to do with the gentiles(they see gentiles under the 7 Noahide laws) https://www.aish.com/atr/Jeremiah-31-and-the-New-Covenant.html
The way they see the blood of Christ I mentioned a few post back but the chief Scripture they will spring on Christians is Proverbs 17:15 https://biblehub.com/interlinear/proverbs/17.htm The reason why is that they will say that you cannot be saved by the "just"(think Jesus) by saying that a just, guiltless Jesus could make you(wicked) clean because both are an abomination(this stumps most Christians they ask). If you have difficulty seeing this I'll be back later tonight but how would you answer them if they said it was an abomination to ascribe all sin on Jesus to justify you from sin.
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