Hi Bobvin,
I'd suggest there are many ways to skin an audiophile... and that we should probably start with anyone claiming to have golden ears or to have the only right way to listen and assess the quality of sound and then also the correlated perception of music within the context of an audio system.
Wow, a great quest though but also a tough challenge to get even an overview into a page or two. I'll throw a few thoughts into the ring but I stress these are just thoughts and are no more validated than most anyone else's ideas.
There is great value in being conscious of how things work but truth be told its really probably optional in terms of enjoying music. Which leads us to determining purpose. If the purpose of the pursuit is to enjoy music it is possible to do it all in the dark of not knowing or completely in the light of understanding... indeed it's possible that training your ears could get in the way of you enjoying the music... nothing seems to get in the way of music more than being in an extended state of analysis.
So to clarify what you would actually like to be able to do... is it to be able to identify and then also express how a component or a whole system sounds. To define and convey the specific effects of what you are hearing and then also the connected quality of experience and to be able to identify what element or combination of elements within the system we could attribute to that experience. Is it ultimately how this affects us in our experience of the sound and also the experience of the music (very different but also clearly interrelated things). Any of this represents a fairly giant challenge and knowing what we are exactly wanting to define is probably an important step along the way.
I can only suggest that for any training you would really need a defined system of assessment and that would be a very great thing for us. First up we could start by trying to define our primary learning outcome for the assessment.
eg perhaps as follows... Outline for a method for a system to assess the quality of sound and the experience of music when listening to an audio system or comparing components.
This is a very different learning outcome for audio training than is say subjectively being able to identify frequency response and or any other typical objective criteria.
There are also a range of states of perception that we need to identify to evaluate as our means of assessment... hmmmm, this is the hard bit. If we are engaged in subjective assessment then understanding our relative subjective state is also probably critical. That is if we listen within a range of perceptual states in terms of subjective assessment then an understanding what state you are actually listening in at any point will be important. Even better if you know how to change your state of perception... especially helpful if you are stuck in analysis... analysis is pretty much like it sounds!
Next up could be about us defining the criteria of the assessment... and also first impressions are important... most of us seem comfortable to start simply out with whether we broadly like something or not (and that is a good place to start). If it is a comparison of gear then also which sound or experience is preferred and or considered overall better and even better still better within specific context (and without any broader range of validation we can only can really define things to be genuinely be better for that listener).
It is also helpful to perhaps start with the sound as a whole and then proceed to break things into their component parts (as we often do) in a range of separately identifiable and broadly recognisable qualities. eg describing the quality and character of bass, midrange, treble, tonality, dynamics, presence, coherence, soundstage etc.
As a suggested way to start all this off is to simply capture and extract key words from the initial experiences of the sound (try to stick to simple words or phrases rather than complex descriptions) like natural, bold, solid, shimmering, liquid, warm, romantic etc. Capture these without questioning and they will help you move forward into further deeper analysis of these qualities somewhere down the track.
For example, say you felt the sound had a beautiful shimmering quality... what does this say about the quality and the extension of the treble. Define this further.
Also if you felt the sound was bold... what is that potentially, does it indicate dynamics, is it about a strong leading edge and well articulated attack, or could it be about an overemphasised mid bass. Try to build a scaffold of understanding as you go and let your experiences help drive the analysis.
Also important is identifying what is best about the sound as well as what is not... identify what is missing. This becomes about identifying constraints and then turning this around eg. I visit a mate and note a quality of sound that haunts me. It might be about a deeper bass foundation, or the relative visceral quality of the sound. So I attempt to give name to that experience and then bring that quality back into the system at home (without losing all the other things I love about the present system). To do this I suppose what seems really key here is understanding how the context of the sound correlates to the experience of the sound. Once we define that connection it enables us to focus on modifying our setup in a more conscious pattern of improvement.
Far out... it would be easy to go further but in the end for me assessment is ultimately about the sense of rightness... and as long as it sounds right I don't really want to think about it to much more, if it feels right do I really want to evaluate it beyond this. Sometimes we like to give name to things but this doesn't always make things better. That is the final point of assessment for me... letting go of knowing.