If you believe Christ did not have deep familiarity with the Jewish scriptures, you should go back and re-read the four Gospels.  At age twelve he was in the temple amazing the learned.  Throughout his ministry he makes repeated references to the scriptures.  He journeyed to his home town and read to the assembled community in the synagogue - choosing to read an Old Testament passage prophesying the coming of the Messiah.  He then told them he was the fulfillment of that prophesy.
He was often with the poor but he was also often with the well-off, living in their homes and accepting their largess.
You are born again not by special feeling but by accepting baptism and receiving a gift of the Holy Ghost.  Once you are a Christian you are required to go and do likewise, not just stay the same as you were before.