It's an interesting point and I think art appreciation operates at different levels.
I'm no art historian nor have I really studied art in any depth. I like what I like and my view of two pieces of the same artist's work can be poles apart. For instance, I like some of Picasso's work but wouldn't have any of his cubist works in my house. Equally, I've seen some photos taken by Martin Parr that I really like but I find others to be like seaside postcards and family snaps.
I don't expect people to agree with me but I don't make my decisions lightly. I'm not even sure that having an in-depth knowledge of art theory or even a specific artist's work will change everyone's views of the artist's work "overall". I suspect that most people will see Michaelangelo's "David" and his Sistine Chapel ceiling and be immensely impressed. Similarly, Van Gogh's "Sunflowers" and "Starry Night". There will be others who won't. Most probably wouldn't be able to name more than a couple of works by any given artist - though they may recognise other work by the artist's "style".
Therefore, other than for those who have studied / are familiar with an artist's body of work, I'm of the opinion that the majority will (rightly or wrongly) make a decision about an artist's body of work based on the artists best known works.
Then there's who's in fashion, how much the piece of art was auctioned for......