How do you know what you're missing?

Without listening to better systems than your own, how do you go about targeting what to improve? How do you know what is possible? It's a case of you don't know what you don't know. I get that indistinguishable from live is the definition of high fidelity, but I don't see that as a realistic aspiration without a dedicated built to spec room and a few orders of magnitude more expensive gear.

Reading reviews or forums can't possibly educate as well as demonstration. "Writing about music is like dancing about architecture," applies to the hardware as well as the media. I've isolated myself for many years prior to current circumstances. I can't remember the last time I actually went and listened to someone else's system. For that matter it's been years since I heard live music, too. (I don't count serenading the cat at home.)

Is it a case of you'll know it when you see it? Is this not a common problem? Or do you just not know it is a problem?
How can you make your system sound like
someone else's system?  Get creative, change things around!

Experiment with changing speaker, listening position.
Experiement with different isolation devices.
Change the furniture and wall coverings in your room.
No need for expensive purchases!

One of two things will happen, with each change. 
Either the sound will improve or get worse.  If you pay attention to
what you are hearing, and really listen critically, there
may be a lot to be learned.  Try a favorite piece of recorded music,
that you know very well.

Adopt a creative, inquisitve spirit, and be open to new exxperiences.

Q: " Without listening to better systems than your own, how do you go about targeting what to improve?"
A: Listen to live, unamplified music. H.P. Called it "The Absolute Sound".
Even the deaf  feel vibrations.....
Life music would be the best, except it depends on acoustics on the venue - from good to very bad.  What about Rock?  Most of concerts I attended had horrible acoustics.  The best seats in Symphony Orchestra are sold only to subscription, while affordable seats are often very bad.

When I had inexpensive receiver and speakers I had to use tone controls often and even with adjustments some CDs sounded horrible.  With better gear I don't have and don't need tone controls.  Most of music sounds good.  It is perhaps because my previous gear had poor frequency response, resonances, distortions etc.
Often cheap boomboxes have equalizers, not only for marketing, but also because they really need it.  So, to me better gear is the one that makes more CDs (or LPs) sound good.  Of course some music has exceptional and some has average recording, but correlation exists, IMO.
I don't think I presented the question well. I'm looking for those subtle things that happen when you change a cable or roll tubes. When doing an A/B comparison it can be fairly easy to pick out which one you like better and maybe even what about the difference you liked. When reading about A and then reading about B and then trying to compare that to what you already have things get difficult. I know it can get better, but I'd rather do more than throw money at it and hope. I want that magical ethereal quality where the music hangs there in the air, leaves your jaw slack, tears welling up in your eyes, and transfixes you as it tugs on your very soul. Maybe I'm just not affected the same way other people are. Maybe I can't ever afford a system that will do that for me. Maybe my room is so god awful I'm slogging uphill with a big bag of rocks over my shoulder. Maybe I need some mushrooms or LSD. I feel like I people are talking about 3-D IMAX and I'm flipping through a newspaper.

Is there a way to truly understand the concept of better sound without experiencing it firsthand? I've had a similar revelatory paradigm shift before, but I know there must be another level. Before spending obscene amounts of money in this pursuit I'm trying to find a road map or set a goal marker. Like I can't get from LA to NY on $14.37, but there's a big difference in cost between private jet and Amtrak. Maybe I'd be better off just settling for a post card.
Actually, I think you did present the question well.

*** How do you know what you’re missing. How do you know what is possible? ***

There will inevitably be push back to this notion, but to know what is possible or, at least, get on the right track to knowing: attend as many live performances that use little or no sound “reinforcement” in a decent acoustic space as possible. Then you’ll know what is possible. You’ll never quite get there, but at least you’ll have a better sense of what direction to go in.
When I tried the Isoacoustic Orea footers, they came with a money back guarantee. The improvements were rather large which I didn't expect them to be.

You won't appreciate it until you hear it in the context of your own system. You'll know and appreciate it once you've heard it.

All the best,

I think your question is a good one and quite understandable.  I've thought every setup  I've  had was great - until I heard something better.  The key is though, you have to hear it.  Either by going to a dealer or another audio persons house, or bringing in some equipment to your place to try it out.  I prefer the latter, either through a local dealer or one that will ship equipment to you for a trial.

If you were to list your equipment here, many of the folks here could offer you an opinion on what might be changed and what that change might do for your overall sound.

I think the same thing might apply if you were to speak to one of the representatives at Audio Advisor or Music Direct.  In my experience, even though that are "salespeople", I never felt any pressure to make a purchase.

Good luck 
Get the gear you are interested in then listen to it. If you dont like it you change it, I went through 5 pre amps before I found the one that gave me the best of what I was looking for. Its a long process that takes some time. Some stores will allow a couple weeks or up to 30 days to return, you might have to pay a restock fee but thats the price you pay for being a tire kicker. I have purchased used equipment and had to resell when not happy but I learned an important lesson too, for the small amount of money lost it was worth it in my opinion.

Matt M
Post removed 
I've heard having friends with good systems helps.

I don't have those, so I can't help you.
I'll bet there are some community bands and small venues for solo players and small ensembles that you could get out and listen to. That would give you a frame of reference anyway.
In all seriousness, you need to approach this like buying icecream rather than a bed.

What I mean is, there's a lot of flavors out there. There's no one perfect flavor for anyone.  All we can do is buy a system that shoots down the middle for our room, our listening habits and the music we listen to.

Having said this, nothing beats experience and finding others who hear like you do, or who at least have a point of reference you can relate to.

Above all, IGNORE prices!! It's just a matter of economics that magazines want to make us believe that the $200,000 speaker is worth $198,000 more than the $2,000 speaker.  Develop your own tastes and be true to yourself.

No reason to get the super deluxe multi-padded bicycle seat if your tush is rock hard and doesn't feel a thing. :)

@cat_doorman, you have posed the question I’ve asked myself over the course of the past 15 years or so since I’ve gotten back into my two channel system. 
The dragon I’ve been chasing is the sound I heard, 16 or 17 years ago at the beginning of my serious audio journey, of a high end set up in an audio shop that seemed to me a completely transparent, three dimensional, gorgeous and mesmerizing presentation. I have no recollection of what any of the gear was, but as I was listening to it, I thought, oh my gosh I never knew a stereo could sound like this, this is what I want.

After that experience I simply picked an element, one at a time, in my system and made a change. When I upgraded my speakers it made a big improvement, when I upgraded my cartridge it made an improvement, when I upgraded my turntable it made an improvement, when I upgraded my CD player it made an improvement, when I went from a solid-state integrated to a tube preamp with a side of the road solid-state amplifier it made a big improvement, when I replaced that solid-state amp with a tube amp it made an enormous improvement. All of this has taken place over the course of 15 or 16 years which has allowed me to afford the changes I’ve made in my system and appreciate each change as I made it.
Live music is always a good experience, and as everyone says, venues play an enormous roll in the quality of the sound. My wife and I have been fortunate enough to have attended quite a few concerts at Disney Hall in Los Angeles over the past several years. Disney Hall’s acoustics are exquisite. Whenever I am in there, I think to myself, this is what I want my stereo to sound like; open, effortless, shimmering, satisfying. 

I found Jim Smith’s book, How to Get Better Sound, very helpful. His main point is to work with your room and the equipment that you have in order to optimize the quality of the presentation and maximize the enjoyment you get out of your system.

if you are fortunate enough to live nearby a brick and mortar audio shop, establishing a relationship with them can be very helpful in this pursuit. Of course that relationship does presume that at some point you are actually going to spend your money to buy some gear from them. In my case, I’ve been working with a particular shop for the past several years and because they know me as a legitimate customer they have been very generous in allowing me to demo gear I’ve been interested in in my home. Some of the gear includes two different amplifiers, a Bluesound Vault and a Chord Qutest dac. I did end up buying one of the amplifiers, the vault, and the dac. I was in the market for all three, but it was so valuable to be able to hear them in my living room.

If you have a friend who is also into this hobby, that can be a great opportunity to hear another system in another real room. As a matter fact I have a friend who is willing to lend me his pair of Harbeth Super HL 5+ speakers to set up in my room while he’s out of town for a couple of weeks. 

And in answer to your last question, what if I’m not even aware that a problem is a problem? I’d say that I was absolutely astounded at how big a difference a high-quality amplifier made in the overall presentation of my system. So in other words, now I am completely aware that everything relates to everything else and everything sounds.

My apologies for the long self-indulgent ramble, but it’s a Friday afternoon, and I have a little time on my hands. Thanks for your patience, and enjoy the music, I know that’s what I’m going to do this weekend!
You have to hear it in your won system  usually having a network where you can each come to the others home with a piece of gear or borrow from a local dealer  Many cable companies all ow you a trial period - musical direct has a trail period

But you don't know what you are missing until you hear it in your own system.

Happy Listening

It's a great question!  Much of the answer depends upon what type of person are you.  If you just want to listen to music and enjoy the experience you won't really worry about how it could be even better.  The music sounds good and you're happy.  For that type of person your question is not particularly important.  There's another type of listener who is more interested in what they call "the journey".  No matter what their system sounds like, they are always thinking about the next step.  It's axiomatic that their system can always be improved.  I suspect they do like listening to music, but they really like listening to their systems.

Once you figure out what type of listener you are the answer to your question is kind of self-evident.  If you're not

Years ago ( mid nineties) when l was in the process of trying to improve my stereo system l had a chance to hear a pair of lnfinity RS lll speakers! Holy ****! they were amazing! The song that was playing was Rodger Millers King of the road. Talk about a bench mark! Another speaker that really impressed me back then was the Infinity Kappa 9's Of course I could never effort either pair back then, but by listening to those speakers it really helped me in my journey to put together a somewhat modest but very enjoyable system that l think has some of the hi fidelity traits of those great speakers
onhwy61 expresses well what one goes through 'getting there', as do the other responders.  What everyone hedges around is the old conudrum:

Age & Experience. (*groan*....'oh, No, not That again....')

What you heard when/where/how/with whom (or not)...what it sounded like that impressed, how it made the back of the neck hair respond (or whatever else occurred)....

The 'I want That daily in my life on demand' kinda thing...*s*

Then the hat trick is to Find and Keep 'That'...because once the stone is rolling it gets harder to Stop and say 'enough'. ;)

Carry a couple of cd's and/or some fav's on your phone with the appropo around....consider what you like about the music you play and what it is that you enjoy about it....

What would seem to make it better; more discrete, dynamic, quiet in the quiet passages, nimble in the complications....

...and keep in mind the space listened within can play as big a role as the equipment...and you as well.

Only you will know the answer(s) to all of the above.

And remember:  All of us have the same equation to solve.

Good luck, and have a good time at it....which IS the point, after all...;)
very good, thought provoking question

i have a few different thoughts it spurs

1) the objective to hifi is not to make it sound like live music necessarily, it is to make it sound realistic, but 'realism' is defined in the eye of the beholder -- so you do need to hear different systems and ideally, have owners describe to you what they feel sounds good about it, and see if you gree (that's why good brick and mortar stores are so important, as well as hifi shows, and local hifi nerd friends and local audio societies etc etc)... i realize these may still be out of reach for many depending on where they live etc etc

2) it is important to try to hear live music in as many form as you can (not amplified), even a street performer singing, playing a saxophone, or a high school performance, or a church choir - remember what the sound of a live voice, a live instrument, sounds like - that purity of tone, how notes rise and decay, no harshness no grain or grit...  is what a good hifi should be reproducing

3) it is easy to fall into 2 traps -

first, that super-clarity and extreme detail is more real and good... that is a 'hifi' creation... real music is not hyperdetailed and disaggregated, it is cohesive and natural; 

second, you should listen enough to define what you like, the sound you like -- don't read reviews or watch you tube videos and let other people define that for you -- for example, some people want their hifi to sound like a rihanna or bonjovi concert... well what you hear at those concerts are huge harsh solid state amps driving huge horn loaded speakers designed to fill a stadium... i would not call that the sound of real music, but you might, and there is nothing wrong with that...

good luck and have fun

I think you are asking a very valid question. After not caring much about music for the past 40 years I’ve jumped into the whole audiophile thing with both feet. I’ve been buying and trying a variety of used equipment. So far I have 3 speakers, 4 amplifiers and 2 preamps with multiple tube options. I’m still struggling with the best way of deciding when one piece of gear is better than another piece of equipment. True A/B testing is somewhere between complicated to impossible and my audio memory only seems to last a few minutes, not long enough to switch cables around. I end up taking notes on certain passages where I think a difference between two pieces of equipment will show up as well as formulating general impressions. All the reviewers that make such definitive and detailed assertions about the speakers and amplifiers they listen to are clearly much more skilled listeners than I am or they simply make that crap  up LOL. I have been surprised at how different the amplifiers sound but I haven’t been able to choose one as being best yet. Most of the tubes in the preamp that I’ve tried over emphasize bass which I don’t like so that is easy. But in terms of what might represent the best, ultimate sound, well I don’t have a clue right now. And then there are funny things where it is hard to determine if a change makes a real difference or if you just want it to have made a difference so you hear your system as being better. I would but my Furman power conditioner into that category. Maybe it made things better or maybe I just wanted it to make things better!
Everything in the following system has been bought based on reading reviews and comments. For like 20 years now. In other words everything you see here. Most recently the Moabs were bought exactly the way you seem to be so convinced cannot work.

Clearly either I know something very, very important- or I'm the luckiest audiophile on the planet. Take your pick. Considering where this is posted, all the comments and history, I'll give you three guesses- and the first two don't count.

As for knowing what to do next, it will help to spend some time reading and studying the System info. I wrote it for a reason.
1) There's an old saying: "You never know until you try."
2) Start small and then work your way up, if you're so inclined. In times like this, we need something to keep ourselves occupied and motivated, so why not music and audio.
3) Enjoy the journey; but, also treat the process scientifically and then analyze the results accordingly.

As you start changing equipment or adding tweaks, one of my tricks is to listen to music in the car first, because there's a different kind of focus and enjoyment involved. Then I listen to it again on my audio system with some additional focus on the details or differences that I perceive from whatever new changes that I've made to my system.
End of the day, it's simply what sounds good to you.

Stay off forums, and enjoy your music. Audiophoolery is just another hobby.
Everything in the following system has been bought based on reading reviews and comments ... the Moabs were bought exactly the way you seem to be so convinced cannot work. Clearly either I know something very, very important- or I’m the luckiest audiophile on the planet. Take your pick.
A third possibility may be the most likely: Confirmation Bias.
In any pursuit, not just hifi, you have to have a clear vision of the goal or call it the target before you can hit it.

If you are asking the question it sounds like you don’t know what the target is in which case one is shooting blindly.

So how to identify the target? Easy, you listen to a lot of things until you can identify “That sound” you want to hear. Both live music and recordings on good quality “reference systems” help. The more you listen the more your brain becomes trained to recognize that good sound when you hear it.

Then the question becomes how to get it in your room? That’s the other hard part.

But the key is to start with fundamentals. Speakers that will work well in your room, placing them properly for best sound, acquiring an amp capable of not just playing them but driving them to their max, a good quality preamp that matches output impedance well to the amp, and of course a good quality source (setting up a phono rig is a whole story in itself much harder than finding a good quality DAC for streaming).

Then from there you might find value in tweaking wires, cleaning up the power, shielding from external sources of noise, etc. YMMV here as well and the differences can range from distinct to none depending.

So bottom line is it takes time and effort to get things right. Hence the hobby.

There are shortcuts to take like buying integrated gear rather than doing it all yourself. For example modern integrated amps may provide a very good quality integrated streaming package these days. Then all you have to worry about is acquiring those right speakers and getting those set up well.

Fun 💰Fun ⏳ Fun!!
good to see miller back to his old form  :)

I appreciate all the replies. Sounds like consensus is there isn’t a substitute for first hand experience. No one has come up with a gear emulator plug in like Pro Tools effects to take your favorite track and digitally alter it to replace your budget consumer receiver with the sound of a top of the line DAC/pre/power amp combo. Just for demo purposes of course. It’s an unrealistic proposition. Damn. I admit I was looking for a shortcut. 

“You can’t get what you want, ‘til you know what you want,” is a common theme for me. Maybe when the world is less scary I’ll venture out and hear something that changes everything, puts me on a definite track.

I haven’t been in a hi-fi shop in about 20 years. I guess I’m just not one of those ride the upgrade merry-go-round types - not that there’s anything wrong with that. They hear a lot more different gear than I have and have already learned their preferences. I envy them, but not enough to follow their example. Other than replacing a few CD players that I wore out (Adcom, Rotel, Ah!) I hadn’t done any upgrades until this past year. I now have an almost entirely new system and am planning next steps. I just want to avoid major pitfalls and am always looking for that thing I missed. Gotta watch your blind spots. We all doubt ourselves at times. Some of us more than others.

I still swap in my older gear from time to time to listen for differences. Maybe I’m a hoarder and I’ll end up with a house full of gear because I’ll never actually manage to get rid of anything. 

Currently looking at some room treatments. I figure that should help no matter what gear I use, and I can add to it incrementally.

Next I’m going move a few models up the Zu line while I’m still inside the 1yr 100% trade in period for my Omen DW. Very happy with them, but obviously moving further up the line will be more of whatever it is I like, right? I will still want to look at different types of speakers, but I need a reference pair. 

Then it will be time for a better pre-amp. I really only got into tubes for the first time this year and have been using a Schiit Saga+ and trying a few tube flavors. I like it better than using my old integrated as a pre. Must be something to that tube magic. I’ve even used it as a tube buffer into my integrated. That was surprisingly successful.

After that I’m not so sure. A better streamer, Class A SS amp, subwoofer(s), more tube rolling, power regenerator, R2R or other types of DAC, and cable upgrades are all possibilities. I may even venture down the vinyl rabbit hole though that will definitely require a demo. That’s far enough out time wise that I’ll need to see what’s out there and try not to be afraid to shop used or change my mind. 

OP: In your latest post, you mention upgrading primary components. In my journey, I’ve discovered that upgrading the power conditioning, power supplies and cabling have tipped the scales from very good to excellent. It was a lot of work - and relatively expensive - but worth it. Just as you described: ’that magical ethereal quality where the music hangs there in the air’. I haven’t changed a primary component in 5 years or so. No need to. In my experience, the key was clean power.

i would say clean power is a necessary, but not a singularly sufficient condition for the excellent hifi sound you describe
Okay. If you say so. I must be imagining things. But, it’s working for me.

not saying you are imagining things... or that clean power matters greatly in your system sounding great

we don’t know the op’s future system, do we? or how much clean power would matter to it...
As I understand it, clean power is a necessary but insufficient condition for great sound. It’s on the list, just not next on the list. I have some reasonable no bullshit cables from Zu and Cullen that should be good until I need to get to the next level. I have an LPS for my DAC. I’m using a Furman PST-8D because it should protect my equipment without completely screwing up the sound. Plugging directly to the wall is never going to happen. Too much at risk. I’ll look into a regenerator or conditioner seriously when I think it has become the limiting factor. 
@cat_doorman I think you are on the right track with power.  In my experience cables and power conditioners will provide you with that last 5-10% and help bring it all together.  Cables are like tires, they link the performance together.  You want to have your engine and suspension tuned before buying performance tires.  If things are out of alignment tires good tires are a waste of money- although you might feel a difference.

You have a very high efficiency speaker. That gives you a lot of flexibility with low powered amplifiers.  There is plenty of light reading out there on what amps pair well with them- that's where I'd start.  That will likely lead you to examine your source.  That might lead you to examine your power, etc. 

You will find out soon enough if you enjoy cycling through gear, buying, selling, trying different sounds, etc.- that's a real part of the hobby for some audiophiles.  If your fortunate, your partner will be accepting of your relatively benign hobby.  If you start looking for enjoyment in the Fedex delivery more than your family, you need to re-examine your situation and what's really "missing".    

As @mapman

"In any pursuit, not just hifi, you have to have a clear vision of the goal or call it the target before you can hit it.

If you are asking the question it sounds like you don’t know what the target is in which case one is shooting blindly.

So how to identify the target? Easy, you listen to a lot of things until you can identify “That sound” you want to hear. Both live music and recordings on good quality “reference systems” help. The more you listen the more your brain becomes trained to recognize that good sound when you hear it.

Then the question becomes how to get it in your room? That’s the other hard part.

But the key is to start with fundamentals. Speakers that will work well in your room, placing them properly for best sound, acquiring an amp capable of not just playing them but driving them to their max, a good quality preamp that matches output impedance well to the amp, and of course a good quality source (setting up a phono rig is a whole story in itself much harder than finding a good quality DAC for streaming)."

A good an introduction as you could want.

This hobby, like so many others, eventually is eventually revealed as no more or no less than a quest for self knowledge and discovery.

Therefore identifying the target (the wish, the goal, the destination, the end stop etc) should be of some interest.

Initially some might find just the journey alone is worthwhile and self fulfilling but eventually that could cease to be the case and impatience and frustration leading to regret might set in.

A better way, I think, is to know yourself first and what you want deep down.

Are you a subjectivist or an objectivist.

Or maybe you’re foremost a pragmatist?

Just how well do you really know yourself?

Bear in mind that this is likely to be a solo journey without much interest from many outsiders.

Who else has the time, the interest, the patience or the resources to assist with someone else’s life journey?

Thankfully, you’re in the right place here to make an educated start.
sgordon1 has said it best.Great comment!!!! 
Post removed 
cat_doorman OP
As I understand it, clean power is a necessary but insufficient condition for great sound.

Okay. If you say so. Good luck!

For those that are interested, having an exceptionally low noise floor with a ’deep black background’ causes a spatial quality of instrument separation - allowing ’notes to float’. In my experience, this black background tipped the scales. It took years of finding the right power conditioning, power supplies and cabling - that synthesized well together. It was a lot of work and very time consuming. Since this is a hobby that I enjoy, the process was quite educational.

When an audio company improves a component - or has several models at various price points - the upgraded versions usually include a beefed up - tricked out power supply. Probably, better wiring, better caps and better internal electrical isolation also. The same approach - only inside the box - instead of outside the box.

Of course, there are many factors involved to optimize a system.  And they’re all valid!  I've been at this for decades. Squeezing out the last bit of high performance is always the most challenging. This is pretty much true for any activity.

you seem to know enough to discern among the various and sundry commentary you are receiving on this post

some folks have strongly held beliefs, right or wrong... sometimes stated repetitively and with blunt force, which, actually is counterproductive to getting the point across effectively

good luck, happy listening
Listen to unamplified live music. 
You said it - vinyl. That will open up a whole new world.
Here is the problem:
An audiogon post is about a general topic,
or a request for information, or even a direction.
People respond with what is working for them,
usually a favorite or new piece of gear.
The responses are particular recommendations,

This can send the poster on a merry go round of
options, taking twists and turns to an unkown

In a quandry over "where to begin," the poster either
may or may not try something new.  But then, how can they have
the reassurance that they are following a path that
will actually lead to better sound?  You have to be familiar
with how music sounds, with what you like, with different listening experiences (good and bad), I believe.

Some typical responses can be, "I like what this guy is saying."
"What if I follow THIS suggestion, maybe this will work?"

"I've isolated myself for many years, prior to current
circumstances."  From your 10/3 post, it looks like there
is a proposed trail of dollars, waiting to be spent.

I prefer to play with the tools that I already have, and keep
the change (no pun intended).  My quest is trying to make sure I am ringing the last bit of musical enjoyment from what I already own.
Under these conditions, a new piece CAN be justified because
I have "paid my dues," and my investment of  time, energy,
and dedication to the pursuit of better sound, is rewarded,
more times than not..

I hope your way works for you.
Read the graphs (frequency response, waterfalls, polars). Then compare them to other speakers.

In today’s market, where it’s almost impossible to hear speakers, much less in a good environment, I wouldn’t buy a critical-listening speaker if I couldn’t see the graphs, or that weren’t recommended by a speaker designer that approaches design from this technical perspective (planars and omni-directionals excluded). Subjective reviews are completely useless to me.
Cat, the sound of any system is a moving target but it does come down to what you hear. Imaging and sound stage are easy to qualify, tonal balance is not. Without a "calibrated" reference it is impossible to know what you are listening to. It is not at all uncommon to see people prefer systems that are way out of whack. A good example is if I increase a systems treble 3 to 6 db over 4 kHz many if not most audiophiles will think this is better. Distortion over a certain percentage is rather obvious and dysphoric. 
This is where good headphones come in. If you are not sure where you are listen back and forth between your headphones and the system. Ideally the tonal balance should be the same at the listening position. 
Describe what you hear as an image in a diary with three program sources that you know inside out. 
Listen to as many systems as you can. The best systems will float an image in space giving you a sense of three dimensions most systems will only give you two dimensions. 
Having said all this, your system is your system and if you prefer it a certain way that is your prerogative.
Others have mentioned comparing a system with live acoustic instruments. How are you going to play live acoustic instruments through your system? Those instruments are going to be affected by the room they are playing in, a situation you have no way of replicating.  
Good systems are always an evolutionary process. So you listen to as many systems as you can. Keeping a diary of your experience is always helpful. The system you liked the best is the one you start to emulate. 
Really an excellent question.  One that I’m asking myself just now.
Being a former musician, I know very much what live music sounds like.
And my system does resemble it closely.
But I didn’t spend real mega bucks [<$20,000) on it. What do systems in the upper five figures and above sound like?  How real is real?
After a certain point are we just chasing minute changes that really don’t matter?
You won’t know what you’re listening for until you hear it.
Upgrade your most "suspect" cable and sit back. It’ll take 2 weeks or more for it to break in and you need to hear what that sounds like. What your favorite vocalist sounds like as break in takes place. Then do it again.
Almost all audio system are never listened to their potential maximum S.Q. by their owner that will never know what they are able to give....

Simple, learn to embed your audio system in the mechanical dimension, in the electrical noise floor of your house, and in the acoustical dimension of the room...

After that most upgrade would become less tentative and often useless if your audio system parts were wisely choosen to begin with...

Upgrading is half the time a reflection of our ignorance about our actual own audio system...

My system value is 500 bucks, upgrading it will cost me too much (more than 10.000) because it is so well embedded now, and anyway i am now happy with it....

Are you able to listen to 9th Bruckner symphony and able to hears all orchestral details and instruments timbre? If yes, your audio system is well embedded and wisely choosen....

Audiophile experience may cost peanuts if you learn how to embed your system.....

Q: If I’ve never had chocolate cake (or haven’t had any in a long time), what are some ways I can insure my recipe turns out as good as possible WITHOUT tasting a bunch of other chocolate cakes or making dozens of trial cakes? What is chocolate cake even supposed to taste like?

A: Try lots of chocolate cake to see what you like. Then reverse engineer the recipe.

A: Make sure to preheat your oven. That is the most important thing.

A: What kind of frosting are you using? The right frosting makes a big difference.

A: Look within to find your perfect inner chocolate cake. Become that cake in the world.

A: You need to use real chocolate. That processed stuff or premixed stuff is no good.  

A: Have you tried cupcakes yet?

A: Try small variations of the recipe to see which you like better. Practice, practice, practice.

A: Go to a baking contest and try all the cakes. 

A: What you really want are brownies. I make special brownies. They’re the best. The secret is in the butter. 


i have absolutely no idea what your point is, but i did just scoop myself some chocolate ice cream

your fault  :)
As @millercarbon says, if you make your system exactly like his it will be fantastic.

If you listen to that malarkey you are not seriously asking the question for advice..
The Jim Smith book, Get Better Sound, helped me tremendously. There are also DVDs that go through all the chapters and expound on what he has written. Very good stuff. He will also answer emails and sometimes talk to you on the phone or Facetime with you.