Finding the 'weakest link' when upgrading?


Being able to find the weakest link when upgrading is really, really important.
Otherwise a different new component may never really be able to show how it is better. Since the other ’weak’ component(s) is(are) masking the new components better sound.

This is a difficult problem.

My best example is not exactly about the least sound quality, but it may show something about it.
I upgraded a good portion of my equipment all at once when I retired. And I still had in my system an old DAC I bought used. When I received most of the new components (including new preamp, new amp, new speakers and a new turntable and cartridge), I was comparing my old DAC with the new one. And found no sonic difference. I mean I tried every way I could and could not hear any difference between them/ So either I just wasted $25,000 for nothing or?? I was very frustrated.
Anyway, after three weeks I got another new bit which had to be ordered and built
.
When I plugged in the phono box, an epiphany and a flood ot tears.. My $25,000 of new equipment really was better. Since the phono box sounded glorious, thus it made it clear all the rest of the system WAS NOT holding back the new DAC. That new DAC was actually just not any better than my old one. And I returned it.

And unless I just happened to acquire that new phono box a week later, I would have been stumped why the new DAC (which was praised to the skies by both Stereophile and TAS) was not doing better.
I was seriously bummed and confused about wasting a ton of money... until I played the new phono box.

Now it was kind of odd that the two DACs, one, used for $250 )it’ original list price was $1,000) and the other $2,400 and 12 years newer) could sound so alike. But chance happened. (And toss in the official guru magazine praise with it all)
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Anyway, how do we find the right part to upgrade? Since making the wrong choice can leave one in the same boat I was in back in my example? (at least until I got the phono box)

I do not have an answer. and I ask.. does anyone?
For me it is just kind of a sixth sense, with little real science to it.

In general I have been kind of lucky.
But how do I know I have managed well?

I do not know.
It has been better more often than not.
(Though I have made a few really terrible choices over many years now and then. Costly choices)

Anyway, my question is how do you make the choice of what to upgrade?
How do you know or decide which is you weakest component?

And do you agree finding the weakest component is really important in the path of upgrading, or one might be making expensive mistakes buying gear, or trying gear? (which may really be great, yet you cannot hear it due to some other weak links in the chain? And though I hate to say so, this weak link may even be cables, or powercords or even the AC from the wall*.

*(but please do not get into a big theory arguments about interconnects and powercords and power conditioners.) Stick to the main topic of knowing how to find the weakest link.
elizabeth
This is, of course, the recurring response when someone says some components make little or no sonic contribution: 'your system is not good enough'.
The counter argument is that there are no measurment data that suggest there are differences above human hearing acuity, and no controlled listening tests. And in my case, I think Quad 2805 electrostats (plus sub) are revealing enough.
@willemj 

The belief that good components make everything ancillary (cables, power, teacups, fuses, magic paste) affect the sound is total hogwash. Only lousy crap components do that. A well designed and well built component should be resolving to the source material and minimize noise and contamination from everything else. Pretty obvious really. Why anyone would want components that are affected by everything other than the source music is beyond me.
willemj
.... there are no measurment data that suggest there are differences above human hearing acuity, and no controlled listening tests ...
Instead of repeated ad nauseum that there is no data, why not collect some of your own? Why not design some controlled listening tests and see where they lead? Of course, that requires a lot more work than just repeating "... there is no data ..."
I love the cognitive dissonance routinely expressed here. When you read the recommendation to “trust you ears” what they really mean is trust your eyes. Once you see the 0.25” thick CNC milled front panel and silky smooth control knobs, you’ll know which component sounds better. And if you ask the “trust your ears” crowd to do a blind test to pick out the component that so obviously sounds better, you’ll get a litany of excuses as to why listening tests are not a valid way to judge audio - LOL.

We were debating the merits of DACs on another forum, one that is more engineering focused. The most strident proponents of DACs sounding different have a commercial interest in designing and selling them. I’m sure that doesn’t happen here.

I read recently that in today’s world opinion carries as much weight as facts. So, as long as you don’t work for Boeing, GE (jet engine or medical divisions), United Technologies, etc, you can believe that fuses have a direction, wire needs to be “burned in”, and that the USB spec for Bit Error Rate is inadequate for audio. No real harm done. Audio is a hobby after all and all you are wasting is money.

On-line readers in any forum have to parse the legitimate and practical from the unfounded and absurd. Caveat emptor applies. You should be skeptical of any on-line advice including this one. For those that don’t have a lot of resources and are trying to get the biggest bang for the buck in their system, even more care is required.

I continue to suggest (as others have) that you spend most of your budget on the best speakers you can afford and skip the amp and DAC upgrades. The distortion in electronics is extremely low compared to the speaker/ room interaction. Once you hit a certain level of design competency and build quality, there is little to no difference in this equipment - none that can be heard anyway.

Well Elizabeth,  I owe you a big apology, I've got your thread Hi Jacked and off on another tangent. I'll respond once and then ask others to open another thread if you'd like to take it further.... 
This whole thing that there aren't performance differences between DAC's.... Where did that come from?  Seems like my words were really twisted.  
So, what I said was "on well designed Dacs"  that the differences are less than that of different designs of amps/preamps etc.... 
I still stand by that.  
Take a EE Dac Mini, A Holo Spring, A Soekris, An Ares, Denafrips and I'm sure others that I haven't thought of.... Great Dacs in their own right.  All Affordable Dacs that would not be embarrassed in any system.  Can you hear a difference, OF COURSE! 
I have myself sat in front of many systems with other people... On person says, "The Difference is Hugh"  another says,  "I can hear it"  
I feel like that when someone wants to hear things that they do and as our ears become more refined over the years that yes,  one person is capable of picking nuances that another may not.  
@douglas_schroeder    Doug,  I read your reviews,  you've earned my respect,  but I have also been in or around audio for 39 years and have rubbed shoulders with granted old timers, but none the less with some of the industry greats.  I've heard many many systems and have come to KNOW that I don't have tin ears and have not needed to question my own judgement for many years. As I stated here,  I think that its easy to over state what HUGE is.  
@bar81   No one said that All DAC's sound the same... 
Again,  On Well Designed Equipment............ 
My own current DAC is a DIY ES9018 DAC... It was ok,  I was a bit disappointed and took it to my old friend Ed Martin from Marcof.  He built a filter network and regulation for the power supply and absolutely transformed this DAC. I would have no fear putting it in any system and being embarrassed, but I'm not delusional that many top notch DACs would outperform it to some degree.... So, not being embarrassed???? are the differences Huge?  To one person yes, maybe,  but to another,  "I can hear a difference".