Correct me if I'm wrong, but even Jesus went amongst the sinners, not the Pharisees.
As an adult! He wasn’t talking to tax collectors when he was eight.
There was a famous slogan running around homeschool circles when I was a kid: “When my son has the faith of Daniel, then I’ll send him to Babylon”.
But he never "stood in their way". My children, like myself, are sinners standing in the Way that is Jesus. Besides, I think that most of the time, the sinners came to Jesus. He never joined them in their sins, he never asked for their counsel or tutelege. He never subjected himself to them as a student or employee, but he brought them to repentance. There is no example of Jesus ever entering the temple of a false god, and he went before Pilate and Herod, only under compulsion.