Just as it is written: “Jacob I loved, but Esau I hated.”
You are confuse undeserving with unconditional. Hitler and Dahmer are already in Hell. Thank God.
“When the righteous prosper, the city rejoices;
when the wicked perish, there are shouts of joy.”
As much as we are humanly capable of judging others to hell.... The hell.. That destroys the soul/spirit has yet to be created. Satan/Lucifer is the only named entity, plus his most fervent followers, (Genesis 6: calls them Sons of God) that to date have been judged to yet future hell.
These that are called Sons of God refused to be born of woman. Christ’s lesson to Nicodemus. All that take this flesh journey have opportunity to ‘see’ the kingdom of God.
The parable of the rich man describes a ‘gulf’ that separates the saved versus the unsaved. The rich man did describe a different type of hell, but that rich man has yet to face the Day of Judgment wherein all souls/spirit individually, will choose life or death.