Prices in puer are often not indicative of quality, I assume wine is the same, but I am not a huge wine guy. I drink pretty cheap wine.
A lot of puer is priced to be gifted, or priced via brand name. I recently had a brand from a Taiwanese "master" - where his blended taidi 2012 Yiwu cakes were well above $100. I would have priced them at about 1/4 of that, in terms of quality or enjoyment. I am sure the tea master knows a lot about puer, but that tea was really average at best.
In some cases, telling the difference between a $25 and a $100 cake doesn't really mean much. I might like the $25 cake better than the $100 cake, does that mean the cakes are priced wrong? Or that I am an idiot? Or both? Who knows?
To the point of your question, I think people who drink puer with regularity can tell the difference between different tiers of tea to a point, and that after a certain point it becomes more about personal tendencies towards certain aspects of the tea. So, probably pretty similar with wine.
Related question, does wine show age as apparently as puer does? Even a relative beginner could identify a 15 year old puer versus a 2013 hot off the press sheng. Is wine the same?