Why is digital audio so complicated? Where did it all go wrong?

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It depends on whether you are judging whether something is an accurate reproduction of the original or just whether it sounds nice to you (which is probably the only thing that really matters)
If you were not the original recording engineer you can not know whether the reproduction is accurate, since even if you are present at the performance as it is being recorded your ears are not where the microphones were positioned, and that makes a BIG difference.

I have been making recordings since the mid 1960s and none of the analogue recorders I used produced an output indistinguishable from the microphone feed.
Every digital recorder I have used was closer to the microphone feed than even the very best hugely expensive analogue recorders.

I worked on record players in the mid 1970s. The lowest distortion pickup cartridge I saw was 2% distortion, and was mono. High quality stereo pickup cartridges often have well over 5% distortion in the mid band and way more at high frequencies. Record players also pick up airborne and structure borne vibration which they add to the cartridge signal. Luckily, the distortion is euphonic and the pickup is a bit like added reverb, which sounds nice.

So, as somebody who has been frequently in a position to compare the microphone feed with the output of the recorder, and worked in the LP business at its height, I can assure you that digital recordings are potentially audibly completely accurate as long as the correct antialiasing filter is used and the ADC is never driven to clipping.
No analogue system is, but luckily (and it is luck not engineering) the shortcomings of analogue recorders, the LP manufacturing process and record players are almost all euphonic and nice sounding.

So good LPs sound nice but they are certainly not and accurate reproduction of a recording and never could be.

If a digital recording doesn't sound nice either the recording was done wrong (ie clipping or no anti aliasing filter) or the microphone choice, or its position (both have a huge effect on the sound) is not to the listeners taste because what comes out of an properly engineered DAC will nowadays be audibly indistinguishable from what went into the original ADC.

Now if a bit of added colour is what somebody likes then LP is a good choice, though the two non-euphonic shortcomings of LPs, speed variation and noise, annoy me a  lot.
To get coloured sound from digital is more difficult. Non-linear DACs, leaving out the re-construction filter and eccentrically engineered analogue stages can do it though

CD standard digital is not quite capable of recording the whole human loudness range from the threshold of hearing to the threshold of pain, but in reality, a quiet domestic room is 30dB, not 0dB so in a domestic situation CD is capable of reproducing everything a human can hear, from the deepest bass to the highest treble, and from a sound just not quite loud enough to hear in a domestic room to the threshold of pain. More than tho other parts of most domestic hifi systems, in fact.

If a high res recording sounds nicer it will almost certainly be because it is a better recording, not because of anything added by "high resolution"-ness.
High res is useful for recording headroom and unexpected peaks but not necessary for playback, although some re-sampling calculations are not audibly transparent so there is a risk in making the conversion.

For me the way digital has "gone wrong" is in its latest guise as streamed files.
Unlike CD and LP there are multiple standards, rather than one, mp3, aac (mp4), flac, alac, wav and so on. Track labelling has not been standardised in any versatile way either IME so I find it irritatingly hopeless for classical music.

Another thing The quality of recordings varies massively. I have fantastic sounding CDs of all ages and terrible ones. I have fabulous sounding LPs and some dire ones too.
IME the difference in sound quality between mediums (and frequently hifi equipment) is less in magnitude than one often encounters between recordings.

So, in summary, after 50 years experience recording, designing record players and being a hifi enthusiast I know that CD can produce an audibly transparent reproduction and LPs can not but that does not mean the recording itself sounds nice.

Nowadays I just listen to music and don't bother much about equipment or medium, CD, LP or streamed file. I sometimes even listen to original master tapes, reel-to-reel, cassette and DAT.

Record players are good for enthusiasts who like playing around with equipment as much or more than listening to music, and I know a few of them...