Paul Griffiths, the Catholic theologian who started his career in the study of Hindu meditation and left it for the Church, is ever the outside the box thinker.
Here he offers us his thoughts on death, which equally apply to Judaism.Griffith looking from the vantage of pietistic works of the pre-modern era asks:Which is more important a good death and journey to the world to come or late 20th century medical care? Seforim like R. Aharon Berachya’s Maavar Yabok from the Early Modern period speak about a good death and a good journey to the world to come.
Is death, human death, a good thing? Catholic teaching is ambivalent about this.
On the one hand, the answer is no: It is a horror and an offense. We make great efforts to postpone it, and we lament when it occurs.
On the other hand, the answer is yes: the body’s death marks a transition to a new condition which we hope will be immeasurably better than the agony of this life; and so it has been a commonplace of the Catholic tradition to welcome death exactly as the gateway to eternal life. The day on which a saint is remembered in the Catholic calendar is her death-day,One way in which this might be done is for the church to educate its wealthy—in American terms, that means anyone with medical insurance and a household income over $100,000 annually—that it might be good for them to die sooner than they do and with less care than they have come to think their right. There is no reason why the church ought to accept the guidelines of the American Medical Association about such things as the frequency with which routine physical examinations ought to be scheduled… Whether it is proper in a particular case will rest upon ancillary considerations, not upon questions about intrinsic propriety.
Another way in which this might be done is to encourage Catholics from an early age in the use of the symbols of death: the skull on the desk, imaginative meditation on the approach and arrival of one’s own death, prayer before the exposed bodies of the dead. These symbols bring the reality of death into life, where it belongs.
I shudder as I write these things because they are so profoundly un-American. These views can be made plausible only if American Catholics begin again to have a sense that there is an art to dying, and that good practice of it means learning when, and when not, to seek diagnosis and treatment. Death’s embrace will come: hastening it is one mistake; resisting it whenever resistance is possible is another.
The Book of Doctrines and Opinions: 
Seems comparable to the narrative about Rebi’s death. Nicely put.
The world may not yet be ready for these thoughts.
Awareness of our lack of control over death supports the human ability (or perhaps, necessity) to confront it. Refinement of medical practices and technology over the last century or so, however, has produced steady advances in our ability to avoid death. The physician, rather than the clergyman, has become the expert consulted at the time of death. And that expert is usually saying “we can control death if we try a little harder” (at least in the long term).
As medical progress slows, it is becoming more obvious what medicine can cure, and what it cannot (e.g., pancreatic cancer is rarely curable). This enables the medical expert to feel more comfortable saying “Death is coming,” and stepping aside so that other practices can begin. Perhaps this is why hospice care has started growing, but hospice is still the exception rather than the norm.
I suspect several more decades of medical stagnation and frustration will be necessary before we become more comfortable institutionally confronting death, and creating useful ceremony for it (rather than just cleaning up the mess afterward).
I think people are ready to hear these thoughts of Paul Griffiths and in the current cultural climate of debating health care spending, perhaps his words are crucial. We need to always remember that it is a tricky balance between embracing life and embracing death. We all want to live as long as possible, but wish and hope that our current physical lives are qualitatively good as well.
In terms of a Jewish art of dying, I think we are challenged to reexplore the texts you make mention of in your post. Most Jewish people are unfamiliar with works like Maavar Yaaboq and of those who are familiar, there is still the challenge of incorporating a 16th century mystical death journey into our 21st century consciousness.
Having said that, working in the field of chaplaincy, it is the works of our mystics that often get lost and when it comes time to people dying, there is little that can be said about the journey of the soul for most were never even brought up to believe in an afterlife. I think we need people to bring to the forefront these issues in the Jewish community for it gives people a hope for something more than life itself. Sure, much of the descriptions of a Jewish afterlife include punishment and suffering along the way, but I think even that people would be willing to hear. I cannot begin to count the number of times I have heard from Jewish people who are dying “do we believe in an afterlife?” My favorite of those was the words of one surviving family member who said, “I envy Catholics for they have an afterlife.” It is very disheartening.