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High-end vs. live sound
Audio systems are typically judged on transparancy, soundstaging, imaging, resolution, etc. Live music doesn't always sounds transparant, rarely has 3d soundstaging or sharp imaging, and sometimes even few details can be discerned. But live music without these qualities still sounds more real and beautiful than a 'perfect' audio system. Maybe there are more important qualities?
Virtual vs. tangible sound
Often it's easy to discern what's coming from speakers and what's happening in the real world. Can a system fool you? Listen to natural sounds and voices around you, make some noises with different objects in your room, that's a valuable reference.
You're system needs to come close to in order to be able to create the illusion of musicians in your room. Otherwise the performance will always be confined to a virtual world, it won't become tangible.
Grey vs. colorfull sound
Real sounds are very rich in texture and you can discern lots of colors. Audio systems tend to sound 'greyish'. Better systems show more contrast, but still sound 'black & white' compared to the colorfull natural sounds around you.
Let's go to the base. What we experience as a single tone from an instument is not just one single frequency, it's a harmonic composition of frequencies (keynote and overtones in certain proportions). We discern different sounds/instruments mainly by this harmonic structure (=timbre=color of sound).
You don't need to a musical hearing to recognise the sound of wood, metal, etc.
Natural vs. mechanical sound
The sound from musical instruments can be enjoyable because of the harmonic overtones they create. In order to reproduce all natural colors and the musicality, a system has to preserve the harmonic stuctures in the recording. As soon as the keynote and it's overtones are shifted in time, it's timbre/color is weakened, it sounds less rich and beautiful, less natural, less tangible, the tones don't 'sing', the soul has gone. You'll get that typical greyish, mechanic, 'hifi-ish' sound.
In an audio system harmonic coherency can be disturbed in many places. Components behave different for different frequencies. All music has to travel through each single component in the signal path, one weak link in the chain spoils everything, so the signal path needs to be as pure as possible. Especially mathematical distortions like Jitter (timing-errors) and digtal filtering disturb the delicate harmonic structures, which explains the typical lack of richness and naturalness some people experience in digital reproduction. Most high-end designers try to achieve a clean sound, they remove the 'dirty' textures, often unaware that they're destroying the harmonic structures.
Adding character vs. reproducing character
Natural acoustic sounds have body, weight, lots of texture but can sound transparant and airy at the same time. They can sound warm, soft, rich but have immediacy, speed at the same time. They can sound organic or even dirty but stay pure and pretty at the same time. They can sound powerful, dynamic but stay relaxed and delicate at the same time.
It are these combinations of qualities that are hard to achieve. When designing equipment towards a certain character, another quality is weakened. The only way to reproduce all these qualities is not to add any character. It's difficult to know/determine what's really neutral, so almost without exception designers choose components that will create the more resolution, tonal extension, transparancy, etc. at the expense of other (initially less obvious) qualities.
(A 'neutral' system means that it doesn't add color, but this term is often misused for equipment that's poor in reproducing colors at all (flat/dull/'grey' sound). A truly neutral system would be able to reproduce all natural colors of a recording.)
Manufacters/designers typically add 'musicality' to their designs by warming-up/softening the sound (often trying to compensate other problems). But true musicality, warmth, emotion, etc. all have to come from the music/recording. Even if you like it sweet, you don't want sugar on everything. A truly musical system doesn't add, it only transfers all musicality from the recording.
Impressive sound or enjoying music?
The tendency in high-end audio has shifted towards spectacular sound, which is understandible, it sells better too. But focussing on superficial qualities will go at the expense of the deeper, initially less obvious qualities.
Often equipment and speakers tend to 'strech' the extremes. Bright and shiny highs (pulsed, exaggerated attack) have to create the impression of more dynamics, transparency etc. A tight pounding bass (overdamped) has to create the impression of more power, control etc. These exaggerations have bring some tonal diversity, unfortunately the real diversity (from the recording) gets masked. When extremes are 'streched', the sound is 'blown-up' and musical performance gets 'teared apart' (harmonic relations are disturbed), coherency is lost. The highs and basses don't seem to come from individual instruments anymore, natural timbres suffer. Tangibility gets lost, especially when transparency is faked.
Another disadvantage of 'streching' the extremes is that less perfect recordings can sound worse than usual (or even unlistenable, aggressive).
Can your system surprise you?
Clear high tones and deep basses should only be reproduced when on the recording. This sounds logical however in practice most systems exaggerate the extremes and all instruments get more or less the same character. You won't be surprised when a new instrument appears. Even systems with a basically high resolution can't reproduce the delicate flavours/timbres when there's too much sauce on top. You might be impressed by such a system at first, but you'll get to know it's sound and eventually there are no surprises.
An honest system will reproduce what's on the recording, instruments and voices appear into your room independent from other sounds. In the long term there's much more contrast and variation. Each recording is a new adventure. But designing equipment for long-term musical satisfaction is difficult, you can't mess with the musicsignal without creating new problems. It's also difficult to sell, usually time and patience are needed before the magic starts unfolding.
Most of us mainly listen to reproduced music instead of live music. Our taste is influenced by 'hifi sound', often audiophiles are looking for a certain sound that doesn't have much in common with live sound. Most people are looking for impressive sound, and most high-end equipment is designed to deliver that. When they hear a honest, musical system they probably won't be impressed.
Are you the weakest link?
But some people find it difficult to find what they're looking for, they are never truly satisfied, at least not for long. Will the next upgrade deliver the magic they're hoping for? How much more do they need to spend? Maybe those who can't find what they're looking for should stop concentrating on sound. Once you forget about sound (overcome the fact that it will never sound the same as live) and you're open to the music, you're closer to the magic. Then a good and honest musical system could even create the illusion of being there, it can be a timemachine that teleports live performances into your room.