How do you paint innocence, spiritual authority, devotion to the Father? The face you've posted looks worried, agitated, frightened and coarse. I doubt such a man would have attracted the Jewish masses as described in the Gospels, let alone willingly and bravely have accepted crucifixion. Can you imagine women washing this artist's rendition's feet with their tears? Would such a man attract the little children--or frighten them away?
Jesus was charismatic, authoritative, imposing--even to his enemies. Pilate was impressed by him. Yet he was gentle, women and children were attracted to him. He was also young and athletic--traveling enormous distances on foot with his followers, living close to the elements half the time. He gave people hope--even the publicans and prostitutes whom the rest of society condemned.
Some of this must have been evident in his face. The shroud, despite the evident disfigurements, is haunting in its dignity. Your artist's picture is a sham, therefore, a deliberate put-down, a shallow interpretation. He got the semitic look right, but nothing else. This might have done as a rendition of one of the Pharisees, actually, or maybe Judas, anguished and tormented as he was at the end--but not Jesus.
Excellent post.
Merry Christmas.