This is one of the reasons Jesus cast off the Jews. They were teaching the doctrines of men. one of them was the after life.
Yes Jesus opposed the doctrines of men, both the errant teachings of the Pharisees and the errant teachings of the Saducees. And a primary way that He did this was through directly teaching against the specific doctrines that were incorrect, and He did so in the language of the day.
As noted before, the Saducees did not believe in the after life and one of the arguments they used to counter the Pharisees' belief in the after life was the argument concerning 7 brothers who because of the Leverate marriage custom/law each sequentially married the same woman after their older brother died without having had children with that woman. The Saducees argued that there must not be a ressurection and after life because such relationships would continue and be too confusing. "Whose wife would she be?"
Jesus countered their disbelief in the afterlife by telling them that they did not know or understand scripture, nor the power of God. When scripture says repeatedly that God is the God of Abraham and Isaac, it not only recognizes that God exists, but that Abraham and Isaac too currently exist though they are physically dead; thus there is life after death. So when it came to the argument between the Pharisees and the Saducees concerning life after death, Jesus specifically affirmed that the Pharisees on this issue were correct; there is life after death, continued existance.
Is the account, at Luke 16:19-31, literal or merely an illustration of something else? The Jerusalem Bible, in a footnote, acknowledges that it is a parable in story form without reference to any historical personage. If taken literally, it would mean that those enjoying divine favor could all fit at the bosom of one man, Abraham; that the water on ones fingertip would not be evaporated by the fire of Hades; that a mere drop of water would bring relief to one suffering there. Does that sound reasonable to you? If it were literal, it would conflict with other parts of the Bible. If the Bible were thus contradictory, would a lover of truth use it as a basis for his faith?
Actually, the phrase "Abraham's bosom" was an idiomatic phrase that was simply another Jewish way of referencing Ga Eden, otherwise called Paradise, what we would call Heaven. As with other idiomatic phrases it is not meant to be taken literally. Idiomatic phrases are common to all languages and cultures. A common idiomatic phrase in the South (itself an idiomatic phrase that refereces traditional, primarily rural, culture in the South-Eastern continental United States) is "burn rubber", a phrase that doesn't literally mean "burn rubber" but to accelerate swiftly. So your argument Abraham's bosom not making sense, well, doesn't make sense.
Concerning whether the story of the rich man and Lazarus was a parable or a true story is, well, not an issue for either way it was intended to communicate truth, it's primary message being that God is just and will just judge us in the afterlife and will take into account not only the suffering that we've had to endure in this life, but what we did with the blessings we've recieved. However, the parable/story also affirms that the then current predominant Jewish belief (Saducees were a minority) that there is existance after life is true. In this parable/story, Jesus assumes the belief that there is conscious life after death, and affirms that there is both comfort and pain.
Concerning the story/parable contradicting other "parts of the Bible", such is a common response that people, myself included, have when a specific scripture evidently contradicts our assumed systematic theology. We can either choose to quickly disregard or explain away the scripture that contradicts our systematic theology, or we can study it indepth to see if maybe our systematic theology is in error in some way. Of course, the apparent message or assumed truths of the story/parable of the rich man and Lazarus does not contradict my belief that there is life after death for all of humanity.
Concerning water evaporating in Gehenna/Hades, as noted before, Gehenna was a then common theological metaphor that referenced the purification of judgment in the after life. The Jews would have understood the meaning, boundaries, and intention of this metaphor. Scripture is full of such metaphorical language and should be interpreted appropriately. To disregard such metaphorical language is to disrespect and mishandle scripture, I believe.
But the Bible does not contradict itself.
What does the parable mean? The rich man represented the Pharisees. (See verse 14.) The beggar Lazarus represented the common Jewish people who were despised by the Pharisees but who repented and became followers of Jesus. (See Luke 18:11; John 7:49; Matthew 21:31, 32.) Their deaths were also symbolic, representing a change in circumstances. Thus, the formerly despised ones came into a position of divine favor, and the formerly seemingly favored ones were rejected by God, while being tormented by the judgment messages delivered by the ones whom they had despised.Acts 5:33; 7:54.
This is the same today.
Concerning Jesus' intended audience, the closest specific group mentioned in the literary context was Luke 18:15, not vs. 14. And vs. 15 mentions the disciples; thus Jesus was not directly opposing the Pharisees. Though I do believe that Jesus was countering a common religious belief of the Pharisees and Saducees that outward physical blessings (riches) imply that one is righteous before God. Such is simply not true. The evidence of being righteous before God is matter of charachter, being filled with the righteousness, love, joy, and wholeness (peace) of God!
Concerning your interpretation of the parable/story of the rich man and Lazarus, of course you're welcome to impose upon it any interpretation you please, but I believe such an imposition is unfounded, not founded in either the literary, cultural, historic, or authorial context.