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?