What does listening to a speaker really tell us?

So, I hear a lot of people saying that the only thing that matters is whether the speakers (and the rest of the system) present a pleasureable experience. I guess what I was saying was that, if you do that, you have two variables in that equation: There is the quality of the performance and recording and the quality of the playback that influence one's experience. If your playback system is NOT absolutely transparent, and what your hearing is NOT a pleasureable experience, how do you know if it's your system or the performance/recording that's causing the displeasure? I would think one would like to put the burden on the performance/recording to meet our needs and use our system to prop them up.

Let me make my point another way, with an analogy. Let's say instead of listening to music, we just liked LOOKING at birds. Well, as it so happens, for one reason or another, we can't always be outside to look at the birds or, some birds don't live around our homes so, we're relegated to looking at pictures of birds when it's convenient for us. However, we do have access to pictures painted by artists who's ability to reproduce birds is so lifelike that we could swear the birds were standing here with us. Now, let's say another artist, maybe Matisse or Picasso paints a bird. Clearly, their interpretation of a bird is NOT reality. However, there are probably tons of people that will get excited over their interpretations and would love to look at their interpretations of birds. But, we can objectively say that Matisse and Picasso are NOT painting pictures of birds; those that we like to see as we would have seen them, had we been there in person. Clearly, in this analogy, the birds are music, the realist artist is the transparent playback system and the impressionist and cubist artist is a "non-transparent" system. I love music. I listen to music in my home because the artists I like are either dead, or not performing in my home when I want to hear them. So, I HAVE to listen to a recording of them. And so, I would like it to sound as closely as possible to the way it would have had I been there at the recording/performance. Thus: Transparent playback system, and the pressure's on the performance and the recording engineer.