After having had a lot of moderately expensive wine over the past few years, I'm sometimes surprised when I go back to a $5 bottle that I like. Usually if I think about it harder, I find that I'm enjoying a combination of sweetness and oak that are pleasant, but not really that fun to dwell on. It's similar to that balance of salt, sugar, and fat that snack foods use to be broadly liked but not have much depth.
Not to say that such wines are bad, but I think you're missing the point to say that expensive wines are supposed to be appreciated by the masses.