If you could afford to pay $100 or more for a "trophy" wine, wouldn't you expect that bottle to be memorable? I had a friend who recently plunked down $125 for a bottle of cabernet that, indeed, was memorable. He described it as "rancid, overbearing and lacking character."
I suppose the lesson here is that expensive does not always mean quality when it comes to buying wine, which is why I always do a little research (usually online) before I spend more than $20 for a bottle.
Conversely, inexpensive wines are not always inferior. In my never-ending quest for excellent wine at bargain prices, I am often pleasantly surprised by the quality of wines I did not expect to be very good.
The point here is that often our expectations are colored by the price of wine.
If the price is under, say, $10 a bottle, we do not anticipate wine nirvana, but we're hopeful that we'll find a good-tasting wine to accompany the comfort food we enjoy on a daily basis.
If the bottle price exceeds $20 or $30, most of us expect the wine to be from good to exceptional so we can pair it with a "Saturday night" meal, such as filet mignon or Chilean sea bass.
Even though we should know better, most of us fall into that trap. Even WineBoy! However, since I do not often spend $30 or more for a bottle, my wine price stereotyping errors are usually on the other end of the spectrum - but they're probably just as costly.
For example, I spend hundreds of dollars a year on lower-priced wines looking for that little gem I can tell you about. What I sometimes discover, however, is that bargain wine (i.e., Carlo's Red at $2.99 a fifth) is a better accompaniment to 4-day-old road kill than to the beans and weenies meal I had hoped to match it with.