This is a very interesting topic. In the final analysis, we all seek to make ourselves happy with our purchases by working to achieve the "sound" that we like. Certainly, I have heard certain systems, some very high end, which, by my standards, sounded awful and had no synergy whatsoever. It is easy to dismiss people who develop such systems as being uneducated listeners, but there may be many personal factors involved. One is human hearing. Even when I was 10-12 years old, I remember that it was shocking to compare the audiometry graphs from those school hearing tests that we all took. There were plenty of young kids with startling high frequency rolloff in their hearing. Another factor is personal taste. If the other guy likes his music ear-bleeding bright, I am not sure he hears it the same way that I do, but even if he does and that is his taste, who am I to say that he is wrong and I am right?
An example of this in the equipment category is Stax headphones, and forgive me Stax if I am smearing you because I haven't listened to your products in over 30 years, but according to my opinions of that time, all their products were extremely bright, harsh and awfully unmusical. I couldn't understand why anyone would want these products nor what relationship this sound could have in anyone's mind to any real or live music. It would be interesting to hear from someone who likes that kind of sound and know what he hears that sounds good to him and whether what he hears has any relationship in his mind to live or "accurate" sound as it exists in a live concert.
This brings me to my another point: Even though we seek to please ourselves first, regardless of the "accuracy" of our components, if live music in our homes is the standard for what we are trying to achieve then there should be a significant attempt to achieve a live music sound, to the degree that this is achievable, in the way we match components and what we purchase. Of course there are fine gradations in approaching what sounds live to any one of us. With regard to the original post on this thread of certain music sounding bad on certain equipment, I am always amazed when a certain recording that I absolutely loved on one system does absolutely nothing for me on another. Often these extreme changes in perception occur just by swapping one component for another (both extremely high quality and where neither lacks in synergy with the rest of the system). Garfish's experience with his migration from Vandersteen 3A to 5 certainly resonates with me, since I am a 3A Signature owner and have auditioned the 5 on several occasions. He is right that the 5 is a very different speaker from the 3A from the midrange up. It is much more airy, open and transparent. It is certainly not hyper-detailed, but it does retrieve a lot more information than the 3A Signature, while it manages to retain a smooth character. I have found that some of the recordings that I audition with don't sound as good on this speaker. Other material, often supplied by the dealer, sounds breathtaking. This breathtaking material sounds ordinary on my system back at home. I've had similar experiences to this after a simple amp, cable or speaker upgrade in my home system. I think Garfish got it right when he says you have to evaluate each system from step 1, applauding what it does well, and taking into account its flaws. If you compare systems head-to-head, it is not helpful to compare them on their individual characteristics. Each must be evaluated as a whole and we can't get too analytical in our comparison that we miss the forest for the trees.
And despite the fact that we each have a sound that we like, whether we know it or admit it or not, I feel that we should keep in mind what live music sounds like in trying to achieve what sounds like real live music to us while balancing that with what sounds good to us. Thankfully, the majority of high end aupdiophiles seem to do this.