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

Zalive, if you do not like the symbals on digital recordings just focus on the bass.

It's really complex, as reproduction is (the way I see/picture it) a multiplication of influences. What's unrealistic with the cymbals or other sounds located mainly in a HF range is a result of not only digital but as well the amplification. Shushurin said a long time ago that the main problem of dominantly used amplification topologies is a total distortion which rises with the frequency, so biggest issues with distortion is expected in a HF range. Bingo, that's where digital has its worst moments too. When distortion and distortion multiplies at some point it easily gets too much and psyhcoacoustics will react: HF becomes more pronounced and easily falls out of balance.

Why I'm saying this: if room acoustics (which is another issue) and amplification quality allows it, system is pretty tolerant to bit of misbehaving on the digital side as there's a headroom of quality reproduction after it and sound is easily full with nice timbre and definition accross the spectrum. So even if cymbals are not perfect it's not a big deal and it's easy to 'forget' it. However if issues multiply too much, you must do some heavy mental self-programming to forget all and enjoy :D and it's not what hi-fi should be about.

Many went to analog rigs I think as they didn't succeed in setting up a nice digital based sound. And it's not impossible to set up a really nice digital front-end system with rich, full and gentle sound. It requires care with the rest of the system, it requires quality amplification, paying attention to details and...if anyhow possible, a solid nice room acoustics (setting up speakers the correct way means 'earth and sky' difference). Because IMO it's the room acoustics which can bring too much focus on a 'digital sound', and make it more relevant than in some other circumstances. 

In the end it's really easy to forget the fidelity imperfection as long as you are able to get the tonal balance completely right. 

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