How much do you need to spend to get digital to rival analog?

I have been at this for over 40 years and owned a Audiostore 
digital has come a long way , the recording has a lot to do with any 
playback , but apples to apples first using Vacuum tubes in digital is a big plus ,on a quality machine tubes distort with even harmonicsare more forgiving natural sounding to the ear ,that being said the Best Buy for the money and is excellent is the new 
Lampizator Amber 3 dac for under $3k none better ,                 enjoy the music.com gave it 5 stars across the board for music quality, instrumental is the cable .i have tried Every brand out there under $1500. Final touch audio Callisto is by far the best in bringing realism to the party. I sold my $6k PS audio dac for the Lampizator , I also bought the $500 Triode Digital power cord it made a very nice improvement all critical components ,and 
synergistic research New Orange fuse. They offer a money back 
trial on Everything including the dac .

As I stated before  key to getting digital right great digital design knowledge 
Lampizator, 2, vacuum tubes bring much more realism to the music ,
which too you can tune to your sonic taste. A top USB cable also is instrumental
i have compared  usb cables up to $1500 and the Final touch audio- Callisto 
is very natural and detailed and at $850 a bargain, and a good power cord.
even the new Lampizator Amber 3 entry lever around $3 k with cable
sound very good  and vinyl at the same price imo is not as good.

how much good ears and good brain cost?

Gallus, priceless.
Zalive, I can still hear fine up to 18 kHz.  I have had many issues with CDs over the years I suspect to various problems with links in the chain.
It is obvious from many albums such as The Trinity Sessions that digital recording can be excellent. I suspect it is the playback process that creates the issues you complain about. Having evaluated many recordings of which I have versions in both digital and analog formats I can say without question that in many circumstances the analog version sounds nicer due to the addition of euphoric distortions. When compared to live acoustic instruments the digital version is more accurate. In many instances that sense of air and depth that many of us, myself included like is due to added distortion. Many interpret that "air" as high end. I have many remastered Hi Res recordings (downloads) that over come the lack of euphoric distortion through thrilling dynamics and more accurate imaging. 
Making generalizations about any format is a mistake and more likely indicates a bias on the part of that individual. There are just too many steps along the way that when not done correctly can pervert the final product in any format.

Mike

Looking back, even BEFORE the Loudness Wars started, vinyl generally has higher dynamic range than its CD brethren. No bout a doubt it. You only need to look 👀 at the Dynamic Range Database to appreciate that. The other big advantage of vinyl, at least potentially, is frequency extension. I’d opine it’s extremely difficult to excavate the intricate data that is contained on CDs for a variety of reasons I’ve covered before many times. It’s a shadow of itself, or what it should be. For CDs, without a whole lot of effort, Air, Sweetness and fullness of bass are usually sub par. Even then.....