Well, first of all, I do not think I am looking at this issue one-sidedly at all. Insofar as the specific hypothetical is concerned ("Would Jesus send someone to prison?") I have based my judgment on what is probably the only directly relevant episode in the Gospel accounts. In this episode, Jesus was confronted with a group seeking to met out the just punishment for a crime He knew this woman to have been guilty of. Although the prosecution's case was warranted in that the woman did indeed commit adultery, it was technically invalid. Instead of joining the prosecution, Christ acted as a skillful advocate and nullified the prosecution's case upon the basis of a technicality. He did not permit the adulterous woman to suffer the just consequences of her action, but rather gave her a second chance in the hope that His Mercy and Compassion, which came to her defence, would inspire her to change her ways.
The verse you bring up bears no such direct relevance, and requires quite a stretched interpretation to bring it bear any relevance at all.
First of all, it concerns the final judgment--the stage where second chances are no longer possible. No matter what crime one commits here on this earth, be it petty theft or rape, there will always be a second chance for that person to repent and be redeemed.
Secondly, it accounts for the final experience of those who have had multiple chances and who have consistently rejected such chances. The chance given to the people of Capernaum was in the form of the miracles performed amongst them, which they rejected. I think i'd be quite within reason to opine that had the adulterous woman continued in her adultery unrepentantly in spite of the Grace shown to her by Christ, that her experience in the end of days would also be less tolerable than that of Sodom.
Lastly, Christ is describing the experience of those in hell as being intolerable, but such a description does not address the question of whether such is experienced simply because it is "deserved." Surely, from the perspective of the righteous man, evil doers do indeed "deserve" to undergo such an intolerable experience, but I could hardly think it proper to ascribe that mode of thinking to God.