Jesus as a teacher would have been both enthralling and disconcerting at the same time. I think being with Jesus would not always have been easy or comfortable. Jesus thought very differently to the people of his time.
When the woman caught in adultery was brought to him they were sure he was going to think the same way as everyone else and agree to have her punished. Yet he does not. Rather he offers her another chance at redemption. This response of Jesus was one which no one expected. Instead of confirming their judgement he challenges the people as to the reality of sin in their own lives. When they see the truth of Jesus’ statement they choose to walk away.
In regards to the woman brought to him Jesus does not condone the reality of sin in her own life either. At the end he says “go away and sin no more.” Jesus displays the difference between indulgence and kindness. Indulgence leaves people where they are. Kindness sees the potential in others and calls them forward despite whatever wrong they might have done. In his ministry Jesus shows that he fully invests in people.
This story calls us to examine our attitude towards forgiveness and warns against judging others with a self-righteous attitude. What it also does is challenge our faith. Jesus did not come to live among us to give credence to every belief we might hold. He sometimes wishes to disconcert us as well. He thinks differently from us so that can gain new insight and thus grow in faith.