vinyl versus digital redux


Has anyone compared the sound of vinyl with the sound of digital converted from a vinyl intermediary ?

I am referring to 'rips' of vinyl made with high end, high quality vinyl playback systems, with
conversion to high resolution digital.
I find it nearly impossible to distinguish the two results.
The digital rip of a vinyl record sounds identical...or very nearly so...to direct playback of the vinyl.

If one has 'experienced' the foregoing, one might question why digital made without the intermediary of vinyl sounds so different from vinyl.   A detective story ?

We are talking about vinyl made by ADC (analog to digital conversion) of an amplified microphone signal and re-conversion to analog for output to the record cutting lathe, or from analog tape recording of an amplified microphone signal, and then....as above...via ADCl and back to analog for output to the cutting lathe.

Of course vinyl can be and is 'cut' (pressings made from 'stamper' copies the 'master' cut in lacquer) without digital intermediary.  Such practice is apparently uncommon, and ?? identified as such by the 'label' (production)

Has anyone compared vinyl and high resolution digital (downloads) albums offered by the same 'label' of the same performance ?  Granted, digital versus vinyl difference should diminish with higher digital resolution.   Sound waves are sine waves....air waves do not 'travel' in digital bits.    A digital signal cannot be more than an approximation of a sine wave, but a closer approximation as potential digital resolution (equating to bit depth times sampling frequency) increases.

If vinyl and digital well made from vinyl intermediary sound almost identical, and If vinyl and digital not made via vinyl intermediary sound quite different, what is the source of this difference ? 

Could it reside....I'll skip the sound processing stages (including RIAA equalization)...in the electro-mechanical process imparting the signal to the vinyl groove ?

Is there analogy with speaker cone material and the need for a degree of self-damping ?
Were self-damping not to some extent desirable, would not all speaker cones, from tweeter to sub-woofer, be made of materials where stiffness to weight ratio was of sole importance ?

Thanks for any comments.
seventies
Orpheus, Mijostyn and Audio2design, I raise this issue because of disappointment with older albums re-released as 'high density tape transfers (HDTT's)' and 'remastered (? EQ-ed up)' recordings.  In both instances the high frequencies are to my ear so compromised as to suspect misleading commercialization.  Certainly, audio2design, audio tape can chemically deteriorate with time, and magnetic information degrades with repeated playback.  To what extent is that information...particularly high frequency information....lost with time even if tape is of high quality and properly stored ?
  
seventies 
I raise this issue because of disappointment with older albums re-released as 'high density tape transfers (HDTT's)'
I've never heard of HDTT. Will you please explain what it means?
In both instances the high frequencies are to my ear so compromised as to suspect misleading commercialization...
What is "misleading commercialization"?
 To what extent is that information...particularly high frequency information....lost with time even if tape is of high quality and properly stored ?
There are too many variables to answer this definitively. It really depends on the tape formulation.
Well this seems to make sense, but am I oversimplifying?

When the artist’s work is prepared for distribution, a vinyl pressing is made and digital streaming files are prepared. The digital streaming files will be identical to the digital mix prepared for distribution. 
The vinyl pressing will be as close as a skilled cutter of a spiral groove can get to it. Close, but never a duplicate. 
Some listeners really like the changes to the original sound that cutting the spiral groove introduces. So much so, that if they want to listen away from their turntable they would rather have a digital copy of the sound the spiral groove makes than the digital duplicate of the original mix.  
And the quality of that copy of the spiral groove can be so good as to be indistinguishable - showing that the ear can not distinguish a digital copy of an analogue sound. 
Is that right?

bluemoodriver
Well this seems to make sense, but am I oversimplifying?When the artist’s work is prepared for distribution, a vinyl pressing is made and digital streaming files are prepared.
Yes, you have already substantially oversimplified. There are many steps involved in "making a vinyl pressing."
The digital streaming files will be identical to the digital mix prepared for distribution.
Not necessarily. CD is limited to 16/44.1, but streaming from a source such as Qobuz can be in hi-res.
Some listeners really like the changes to the original sound that cutting the spiral groove introduces.
Again, you have substantially oversimplified. It is possible to make an LP that is very, very close to the master tape. That’s why test pressings are part of making an LP.

Digiphiles often chime in here with claims that digital has better s/n and dynamic range than LP can ever have, which is true. But that advantage is often way in excess of the what the music actually requires. That’s a big part of why an LP can sound so close to the master tape.
Cleeds, bluemoondriver, 
Apologize if I did not clarify.
I concur that lp's newly made from tape or high resolution digitalization of an audio source can be 'very close to the master tape' except that 'cutting the spiral groove' (what I termed an electro-mechanical process) changes the 'original sound' in a manner pleasing to some listeners.
I am asking about LP's made decades ago from analog tape...whether these lp's preserve sound...particularly high frequency sound...better than does the tape itself.
Regarding possibly 'misleading commercialization', I refer to 'high resolution digital transfer'...ie transfer from tape... and 'digital re-mastering of tapes recorded decades ago....before high resolution digital recording became available.
One company, 'High Definition Tape Transfers' (HDTT is their logo) offers downloads in a choice of digital resolution.  To my ear 'high resolution' is a specious claim insofar as one is making a high resolution digital copy of a time-degraded source....ie. low resolution in particular respect of lost high frequency information.
Digitally "re-mastered" tapes from that era, also sold as downloads or streamed, and sometimes not identified as 'remastered', are subject to the same loss of initially recorded information.  Resolution is not and cannot be improved by boosting the treble.
Am I misleading ?