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1. Is there an audible difference between $1000 and $5000 dac? And if there's a difference, how much?
2. Is there an audible difference between 24/96 and 16/44.1? And if there's a difference, how much?
3. Assuming either 1 or 2 is true or both are true, what is the "right" way for people to buy dac's and/or cd's?
There are two categories of audible differences.
Differences in the delivered sound, that cause differences in what we hear. They are measurable, and quantifiable.
Differences in what we hear that are not caused by differences in the sound. They might be called "psychologic", though their belonging to the field of psychology, physiology or neurology is another debate.
Both differences look exactly the same to our ears. Only some advanced practice of double blind testing allows, in some case, to distinguish between the two.
So about question one,
-There are often differences of the first kind. High end audio is a domain where many, if not most, electronics are "coloured". Their measured performances are usually very bad. Amplifiers with THD between 1 and 10 % (more than 10 % for the most expensive amplifier in the world). I cited some sources of such differences above : mostly non-oversampling, and tampered digital filters.
How much ? Just plot the frequency response of said DACs.
-Differences of the first kind are nearly non-existent between 24/96 and 16/44.1. How much is "nearly" ? If you crank up the volume to insane level in the absolute silence, you can hear the 16 bits quantization noise.
-Differences of the second kind are extremely versatile. They vary from listener to listener. Some listeners hear no differences between nearly anything, while other hear differences between everything. They can vary according to the time of the day, the weather, anything... One of their most important characteristic is that they are not quantifiable in the same way as differences of the first kind. The most common measurment unit is the "night and day".
For convenience, we might call them differences in "musicality".
About question one and two, I'd say that differences of the second kind do not depend on what is tested. The fact that DACs between 1k and 5k are considered, or 24/96 vs 16/44.1 has absolutely no importance for these differences. It's an alchemy taking place between a listener and a concept. The concept of $ 5k DAC does not mean the same thing for all listeners, therefore they do not experience the same amount of 2nd kind differences between them.
-What is "right" ? Depends on what "right" means to the listener. Some, called "objectivist", think that 1st kind differences are right, while 2nd kind differences are wrong, and thus blind listening tests are absolutely necessary in order to know what is right and what is wrong.
Subjectivists think that both kind are right, thus blind listening test are completely unuseful.
Most of the audiophile don't fall in these extreme category, and while all of them agree that differences of the first kind are right, differences of the second kind are not really dealt with.