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Which would Epicurus choose?
At this particular moment, despite my poll answer above, I think I'd choose the shepherd. Partly I'm choosing avoidance of pain 
. But I'm also considering that learning and growth bring me great joy, and the shepherd is probably closer to my stage of growth, which perhaps would give me the space to enjoy the pleasures of nature and experience the process of growth.
However, the option of Epicurus' final week could serve as a trial run for my own death (not that I anticipate dying in that particular way: more a trial run of the process of dying) and as such could be of value and interest.
Having now answered a hypothetical, I'm turning and running from the rabbit hole as fast as my legs will carry me!
Which would Epicurus choose?
That is a very good follow on question to help articulate the answer to the first and main question: Would Epicurus himself have traded places for the week that is under discussion?
I think this poll should be very interesting and after we see some commentary and look for fine tuning I am going to put it on the Facebook group!
The Grecian are youthful and erring and fallen gods, with the vices of men, but in many important respects essentially of the divine race. In my Pantheon, Pan still reigns in his pristine glory, with his ruddy face, his flowing beard, and his shaggy body, his pipe and his crook, his nymph Echo, and his chosen daughter Iambe; for the great god Pan is not dead, as was rumored. No god ever dies. Perhaps of all the gods of New England and of ancient Greece, I am most constant at his shrine.
It's interesting that while Lucretius records that magnets were so named because they came from Magnesia, Pliny the Elder quotes Nicander of Colophon as suggesting that magnets got their name from a shepherd named Magnes, whose iron studded shoes stuck to the ground on Mount Ida.
I chose option three.
As a human (like other animals), I do desire to achieve pleasure and to avoid pain. So of course I will choose the option with no pain. However, if I do end up the same way as Epicurus – dying from bladder stones or something else painful – I may choose instead to accept my impending demise knowing that I have lived a good life. If I can remain as cheerful as Epicurus was in his last days, I probably wouldn't think of any other option.
That is a very good follow on question to help articulate the answer to the first and main question: Would Epicurus himself have traded places for the week that is under discussion?
Assuming that in this hypothetical Epicurus avoids his painful death, I would say no but only because it would allow him to prove that he can still be cheerful despite being in pain, setting an example to his followers. His body may have been in immense pain but his mind wasn't as he was able to remember and reflect on his life, his friends, his philosophical discussions, etc., which gave him pleasure. And of course he knew that he wouldn't have been in immense pain for too long (PD4). Not to mention that he also had people who were capable of tending the Garden after he was gone. Preserving his legacy and teachings for generations to come... until Nature decides to bury a lot of it under ash and lava. Maybe building a town near a volcano isn't a good idea?
It seems that this hypothetical could be made more simple and clear. And there could be multiple ways to do so. For example:
"Would you rather be Epicurus, living in pain on your deathbed surrounded by friends knowing that you have made great contributions toward understanding the nature of the world and helping others understand it as well"
or
"Live your last week on earth pain-free but all alone on a mountain as a shepherd, and then have a very quick death from a sudden heart attack from eating too much sheep cheese, AND leave no legacy."
The original hypothetical as stated in post 1, sheds light on the natural desire for good health (and why so many picked the shepherd), since the wording of the hypothetical was such that the shepherd was not in pain.
We cannot control what kind of death we will have, or if we will be surrounded by friends or die alone. AND this question: How much can we control what kind of legacy we leave, since a portion of that process occurs by chance?
I was assuming I wasn't dying at the end of the week as a shepherd.
Personally, I think being a student of Epicurus for a week, even his last week, is more intriguing than "being" Epicurus himself.
And on the topic of being a student of Epicurus for any time period, here is something I think is related that any student of Epicurus should consider:
Q: "What is your understanding of Platonic Idealism and Aristotelian Essentialism and how they may or may not relate to Epicurus' view of Pleasure? Does considering that relationship (if any) indicate anything as to how you would answer the question being posed?"
Agreed. Unlike so many Christians, whose understanding of their Savior and the depth of their knowledge of the Christian tradition is self-mistaken for a projection of individual wants and desires and fears based on nothing but their own, personal experiences, and limited educations related to religious history and comparative philosophy, it should be important for us to not believe that we think we understand Epicurus, and mold our understanding to the needs of our own lives, but rather to make a commitment to understand the texts as they are, not as we are.
And then, when teaching new students, we simplify the teachings to a genuinely accurate (though incomplete) summary.
Personally, I think being a student of Epicurus for a week, even his last week, is more intriguing than "being" Epicurus himself.
Which leads me to ask if a more difficult question would be:
You can travel back in time for one week (and you're able to understand and read the language, have all the proper inoculations, etc.) for a specifically Epicurean excursion. When and where do you go?
Do you spend a week:
- sitting with Epicurus as a child, badgering his teachers about the origins of Chaos
- learning with Epicurus in Lampsacus at the beginning of his philosophical work
- traveling with Epicurus when he was getting kicked out of Mytilene
- being with Epicurus during the last week of his life
- in Athens meeting with Cicero and Atticus and visiting the Garden, Academy, etc.
- visiting the Villa of the Papyri, reading in the library, and attending a 20th with Philodemus and Piso
PS. I'm intentionally leaving out spending a week living in the Garden and house with Epicurus in his prime, in the mature school surrounded by students. That'd be the easy choice for me.
For me that one is easier I think - I would want to be able to question Epicurus in his most mature and advanced stage of life, so I would say "being with Epicurus during the last week of his life" to ask him where he eventually came down on many of these same issues we are discussing.
And i would probably include the exact question we are discussing from post one of this thread.
Ah! But how readily available would he be available that last week? How open to questions? How bedridden and in pain would be be? How much wine was he drinking to dull the pain? I can come up with all kinds of complications! 
I can come up with all kinds of complications!
I knew the Don we all know and love as to hypotheticals would not be long in coming!
