Writing this made my brain hurt, so I'll view and reply to more of the thread at a later time.
Wilkey-
If a $12 bottle has the same utility as a $120 or $1,200 bottle, then what makes the latter possible, desired, and perhaps even generally considered superior?"
If the humble, freshly rolled, freshly smoked cohiba of the Mesoamerican and Caribbean peoples are the authentic roots of the modern day cigar, then how authentic is a $27 limited release?
Now transpose the questions of utility and authenticity across the two examples.
In my mind, neither wine nor cigars have, on their faces, any particular utility at the basest level. Water is, I think, a better tool for hydration than wine. As a form of sustenance, grape juice, with most of its sugars still intact, seems superior. And tobacco has no use in providing sustenance, shelter, or reproduction (the post-boink Marlboro is a modern invention, and not a neccessity

).
If you view aids to pleasure and relaxation as utilitarian, then the increased level of pleasure and relaxation a finer cigar or glass of wine brings leads me to believe a twelve dollar bottle or 2 dollar cigar doesn't have the same utility as its more expensive counterpart, provided that the more expensive choice brings more pleasure and relaxation. This is not always, but often, the case.
Regarding authenticity, I ask the following:
The science of mathematics likely started using fingers or pebbles as tools. How authentic is a Cray Supercomputer?
Man likely first fought with his fists. How authentic was the horror that fell from the belly of the Enola Gay?