Jesus never disagreed with "The way of life is above to the wise, that he may depart from hell beneath."
What he said about no man having ascended to heaven does not contradict Proverbs 15
No one has
ascended into heaven except he who descended from heaven, the Son of Man.
As to the meaning of Sheol.
I know that many believe and repeat what you posted about Sheol. I get that. I used to repeat it to because I read it in books.
Then when I started reading verse by verse study with commentary helps I learned that it is not the most popular view among the scholars. It turns out that more of them think that Sheol was understood as the place of the wicked dead and these verses you posted do not say that they thought that all people go to Sheol and it is sorted out from there.
It does not say that Sheol can be translated as Grave either. This came from interpreting these texts not from translating the word. The word itself does not mean grave.
That came from thinking that is what Jacob meant or what Job meant. But what if they meant that place where wicked people go. Jacob thought he was under a curse of judgment and expected Sheol is where he was going when he said that. (or it is possible that is what he meant)
Job straight out said he was under judgment and thought he must be going to hell and so what he says about hiding him in Sheol has the background of him judging himself as a sinner under judgment in previous rantings.
So none of these verses prove that Sheol should be translated Grave or just some nuetral place. And this is what the scholars talk about.
We have been told things that have not been clearly proven and we repeat them as fact.
If one takes the time to read each of those verses and if they think "what if they were thinking of hell" then one can see that it fits most of these verses and the tenor of the speaker much better than what they might have realized before trying this exercise.
Sometimes we do well to put aside assumptions that make us read into a text what it did not say. Grave being one of them.
Realm of the dead fits, but it fits even more if one sees it as the realm of the wicked dead.
This seems to be the better hermeneutic but I still have more study to do on it. I have put it on a shelf for now.
I am just no longer convinced that it should be read as Grave or just realm of the dead for everybody and God sorts it out later meaning. That no longer seems like the intended idea now that I have read what these scholars are saying about it.
There is a good article on it that I will try and find again. It was well done and included lots of footnotes and references and I planned to dig deeper. If I can find it again I will post it.
I am not trying to change your mind about what you believe about it. I am just interested in this as a good CC topic because it is one of those that has the potential to open a lot of minds to the subject of hermeneutics and how to discover authorial intent.