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So are we to believe that Jesus... trains his chosen people to repent and obey, but then pulls a switcheroo on them in the NT?

Apparently, this is what Dispensationalism teaches. It is a twisted theology (albeit not as evil as the Supercessionism of the Catholic Church, or the Reformed movement). Ironically, both Supercessionism and Dispensationalism lay the guilt on the Jews of the "Old Testament" for not faithfully following the "Law of Moses" - but then in the "New Testament" claim that it is not operable. What arrogance!

They have to play disjointed hermeneutical games to create a systematic theology - that cannot treat the Bible as a unified whole, able to be read literally. No wonder Jews shake their heads at these theological contortions.

There are many difficult things to understand in Scripture. Obedience is not one of them. It is clearly, and plainly spoken of by the mouth of the Almighty.