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
To my own ears of having always been around, for instance, REEL TO REEL tape; IMHO:  24-bit and DSD remastered cds come A LOT closer to sounding like an original 1960s copy of a quarter-track, 7 1/2ips vintage commercial tape (in terms of: capturing soundstage width as well as bass response, especially) than vinyl ever could.  The characteristic upper bass/lower-mid bloat peakiness OF VINYL sounding like a phase-distorted bathtub affect is the thing I, personally, have never been able to stand about "vinyl sound".  Of course, someone restricting the debate to records vs.: (badly mastered) 16-bit cds, computer audio, streaming, mp3's, etc. won't recognize that and therefore think vinyl (beholden, by default, to being a "component grade" audio medium) is the top-of-the-heap....BUT: it's a disingenious argument when the buyer DOESN'T know what was considered above LP playback when there was no digital (and, too: when records were a mass-market $5 item and not a $40-up boutique novelty).

The wild-eyed claims of vinyl's frequency abilities also prey-upon the uninformed (and: always seem to be spoken by snake-oil hucksters selling $20k turntables!).  Truth is: THOSE specs came from JVC's parameters for reproducing Discrete Quadraphonic records in the 70s; requiring a Shibata stylus and an outboard demodulator to "unscramble" a 30khz subcarrier pilot signal containing rear channel matrixed information (which, as a sidebar: if anyone ever experimented with such arcane gear for fun, even a quality rtr deck was able to register the quad beacon "birdie" while recording at 15ips....even the single motor Panasonic/Technics model RS-736 rtr I had from my father in 1972).

If one is NOT talking about the obsolete tech of quadraphonically-encoded records neccessitatingly played back with a Shibata stylus, then all of vinyl's far-flung frequency specs are totally irrelevant and a moot point.  Vinyl, for one, is THE WORST for Classic Rock in STEREO.  Much too hollowed-out.  The 1969 Ampex 3 3/4ips reel of Led Zepp II, for example, is the next best vintage source to the Ludwig first pressing(!).
Raulirugas, 4trackmind and others, I appreciate your comments and....unless I 'missed something'....agree. 
1. 4trackmind, could you please clarify: in stating that "24 bit and dsd re-mastered cd's come a lot closer to sounding like an original 1960's copy of a quarter track....", do you mean that they sound as did the tape recordings when whey were
new, before time and playback had taken their toll of the sonic information ?
2. Regarding DSD vs PCM, and in the context of 'DSD re-mastered CD's, and assuming that DSD-PCM differences hugely diminish at the highest available digital 'throughputs', are you tempted to broach another subject:  Do DSD 64 (not 128 or 256) and ?? RSR 'ladder' DAC's smooth lower resolution digital sound such that it, like vinyl' is more palatable even if less 'realistic' ?
Thanks again for your thoughts.
4trackmind
... The characteristic upper bass/lower-mid bloat peakiness OF VINYL sounding like a phase-distorted bathtub affect is the thing I, personally, have never been able to stand about "vinyl sound"...
That "characteristic" isn’t inherent to LP playback, although it’s surely common with cheap and/or poorly aligned equipment.
The wild-eyed claims of vinyl’s frequency abilities also prey-upon the uninformed (and: always seem to be spoken by snake-oil hucksters selling $20k turntables!) ...
Please tell us what $20K turntable you think represents "snake oil."
If one is NOT talking about the obsolete tech of quadraphonically-encoded records neccessitatingly played back with a Shibata stylus, then all of vinyl’s far-flung frequency specs are totally irrelevant and a moot point. Vinyl, for one, is THE WORST for Classic Rock in STEREO. Much too hollowed-out. The 1969 Ampex 3 3/4ips reel of Led Zepp II, for example, is the next best vintage source to the Ludwig first pressing(!).
Those tapes sound awful. In addition to the limitation imposed by the slow tape speed, those commercial releases were dubbed at high speed, so any high frequencies that might otherwise have survived tape saturation don’t even have a chance. Even a 7.5 ips commercial tape can usually be pretty easily outperformed by a decent LP and turntable.

Don’t get me wrong - I like tape. But just as with LP, its performance potential is often not realized. And tape has its inherent challenges - including properly aligning bias to tape when recording, and of course HF saturation, EQ and tape head alignment.