The hypothetical scenario reminded me a quote by John Stuart Mill that probably you know: "It is better to be a human being dissatisfied than a pig satisfied; better to be Socrates dissatisfied than a fool satisfied."
For Mill there are special pleasures, like reading philosophy, listening to music, contemplate art, etc., that are superior to other pleasures (accesible only for animals). I understand his idea, but I reject it for similar reasons why I reject stoicism: I don't think there are intrinsically nobler people, nobler activities or nobler ways to live (or intrinsically pleasurable).
I do think there are standards to evaluate pleasures and pains among people but they're not necessary, but contingent. (After all, we are human beings, of course we share plasures and we share the absence of pain as a goal to achieve.) Cassius, I think you won't find an activity that brings pleasure in all contexts: human nature it's not about immovable truths but about change.
Finally, I know the Letter to Ideomeneus is beautiful and inspiring, but I really doubt Epicurus was really having pleasure in the previous moments of his death. So, if I had to give an answer, I'd prefer to live like the shepherd, but better I prefer to be me, in this place and this time.