The preponderance of the evidence is in your favor, and I think the KJV translators did us a disfavor in translating both "Sheol" and "Gehenna" as "Hell".
True, translation, (or should I say ‘mistranslation’) has a lot to answer for.....but according to the Bible it is not surprising.....men were already “twisting the scriptures”.
“But according to his promise we are waiting for new heavens and a new earth in which righteousness dwells. Therefore, beloved, since you are waiting for these, be diligent to be found by him without spot or blemish, and at peace. And count the patience of our Lord as salvation, just as our beloved brother Paul also wrote to you according to the wisdom given him, as he does in all his letters when he speaks in them of these matters. There are some things in them that are hard to understand, which the ignorant and unstable twist to their own destruction, as they do the other Scriptures. You therefore, beloved, knowing this beforehand, take care that you are not carried away with the error of lawless people and lose your own stability.” (2 Peter 3:13-17 ESV)
So if it was happening back then and the foretold apostasy kept gaining momentum, it would only go from bad to worse, as what became “Christianity” sank to alarming levels of abuse of power.....torture and murder in the name of Christ. We all know what history reveals about the conduct of “the church” during 1500 years of tyranny and control, basically dictating to the rulers of the day. This kind of power “corrupts” which is why Jesus taught his disciples not to imitate the Pharisees....
“8 But you are not to be called rabbi, for you have one teacher, and you are all brothers. 9 And call no man your father on earth, for you have one Father, who is in heaven. 10 Neither be called instructors, for you have one instructor, the Christ. 11 The greatest among you shall be your servant. 12 Whoever exalts himself will be humbled, and whoever humbles himself will be exalted.” (Matthew 23:8-12 ESV)
Jesus was humiliating those who exalted themselves, and who were treating his disciples like despised, worthless human trash. Jesus gave these ones dignity and hope.
The one piece of the puzzle that doesn't fit is that Jesus used the word ᾅδης, "Hades" to describe a place of conscious torment in the afterlife (Luke 16:23). While context here is just a parable, the parable probably reflects the common understanding of the people in Jesus's day. What changed between the OT and the NT?
Parables are illustrations, not true stories with real people, though based on the characteristics of real people, easily identified. Understanding the characters in this parable you can see what the lesson was....
The rich man represented the Pharisees and the beggar represented the “lost sheep of the house of Israel” to whom Jesus was sent exclusively. (Matthew 15:24)
We know what Jesus thought of the Pharisees and he castigated them continually for being woeful shepherds of the “lost sheep”, whom Jesus’ illustrations showed were precious to his Father and that they should have cared for them, but instead demonstrated their complete contempt. (Matthew 23)
In this parable, Jesus indicates a change of place, illustrated by their deaths. The Pharisees were now on the back foot with Jesus preaching, exposing them for the religious frauds and hypocrites that they were. The torment was from Jesus’ denunciation, and now the beggar was in the position of favour illustrated by “the bosom of Abraham”. The “bosom” is where a person of favour reclines at a meal. The apostle John was said to recline in this position at the Last Supper.....
“There was at the table reclining in Jesus’ bosom one of his disciples, whom Jesus loved.” (John 13:23 ASV)
The “bosom of Abraham” was a position of favour with God. This parable has nothing to do with any real life situation, but using a real life situation to demonstrate a spiritual situation.
The Pharisees “died” to God by being exposed by Jesus.....whereas the ones of the “lost sheep” whom the Pharisees had judged as not worthy of their time and attention, now gained the “bosom of Abraham” as those who accepted Jesus as Messiah.
In their spiritual death state, the Pharisees were becoming desperate because Jesus was having an enormous impact on the people to whom he preached. (Matthew 11:25) They then plotted his murder.
The parables Jesus gave were about familiar things to his Jewish audience. In their scriptures, conscious life after death was not taught. Under Greek influence however, the Jewish leadership had adopted the Greek notion of an immortal soul. “Sheol” somehow became “hades” a place of conscious existence and suffering after death. Yet their scriptures taught exactly the opposite. (Ecclesiastes 9:5, 10) Sheol was a place where there was no conscious existence.
So Jesus, in using hades in his illustration would not have drawn on a false religious teaching. But used death as a way to demonstrate a change in status of those who once held that position of favour who had now officially lost it, and the despised spiritual “beggars” had gained it.
To take this parable literally, it makes little sense, but to understand the symbolisms, it makes perfect sense.