I can very much sympathise with your "battle", as in many ways I have gone through similar myself: the difference being that in my case I was able to reach a positive, rather than negative outcome, with what would be considered pretty ordinary equipment, playing very ordinary CD's; others have seemingly achieved similar results. I will just repeat what I have said elsewhere that I have experienced very expensive, highly tweaked, at home vinyl setups that have sounded a) stunning, and b) excrutiatingly harsh and unpleasant, so I certainly am aware how there can be two ends of the scale, irrespective of the time and money spent.
The answer, to repeat myself, is system engineering, and yes, in digital it can be much harder to get it right, compared to vinyl, but superb results on that "nasty" 44.1k digital CAN be achieved.
Finally, a "thought" experiment. I would suggest that your own system, in top form, be modified by the addition of a black box completely hard wired in, with a bypass switch. This would be engineered so well that it would be 100% transparent with the bypass engaged (unlike how all these DBT setups most surely are typically set up,) to yourself and anyone else you care to have listen. In the black box is a "done right" 44.1 analogue to digital converter feeding a 44.1 digital to analogue converter, engineered CORRECTLY with current technology, and, you can guess what's coming, I would seriously suggest that the people listening would find it close to impossible to pick when the extra circuitry was part of the mix ...
I appreciate your passion, I felt that way at one time a good many years ago.
As time passes you realize it's a delusion that you can make a difference and then get down to the business of making music the best you can with what really works and what is available instead of just wishing.
I am friends with a good many people in the business, have completed advertising photography for dozens and dozens of high end brands, both analog and digital.
The short answer is, only long term listening can reveal what is really right and what is not. Digital can be "good" but never the level of analog master tape or LP at its limit.
Over the years we have had duplicate copies of both CD and LP and compared with many brands and quality levels. If you get LP reproduction poor enough and digital good enough then digital can make a good showing.
If you have analog at the best it can be and digital the best it can be then analog wins unless there is an extraordinary (bad or good) copy on both sides. I can't cling to the <20% times when digital makes a "decent" showing for an investment of $25K +.
Over the last few years I've worked hard to accumulate master tapes. I had my Studer rebuild two years ago by the (previous) head guy at Studer USA. You have no idea what this machine can do, it will scare the hell out of you sometimes and set your head straight as to what is possible.
My turntable when it's maxed out at 100% can get maybe 80% (+) of what the tape is doing. The CD is not worth comparing at that point, believe me.
Also, read this (partial) post of mine on this same thread nearly three years ago. It's still very much true and why I sometime come off as angry.
I've had at least a hundred thousand dollars worth of digital through my system, most on loan or product that was a perspective item for review. I also bought a lot.
When a promise is made over and over and disappointment follows there are a couple of reactions a person can have. Sadness that it's not what you were expecting, and later (after the same things happen fifty times), anger that you were taken advantage of.
I've had this enough times to be angry, I've given up on digital other than for background or breaking in components. Happy for others that have made it work, perhaps we hear differently or it's a system thing.