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
I am not sure, who is this listener what hears exactly what is "objectively better" - ? And I am sceptical to such claims regarding digital. It is not as if I have not tried. I played analog for many years, until I switched to digital, naively thinking "a bit is a bit". It wasn't. I had to reinvest in my analog chain, to get better sound. I think some of the confusion here is due to differences in the quality of the analog chain. It has to be fairly good (but not outrageously expensive) to compete with the best digital.
Now, I've recently invested in a Teac NT-505. It does raise the digital sound quality quite a lot, in my case, going from a Squeezebox. Very enjoyable. So I've been listening to streaming (masters from Tidal) and to hi-res recording over the home network. The Teac is a bit polite maybe not fully burned in, but very nice. Then, last night, I put on the latest Blue Oyster Cult, The symbol remains. 2 x LP. Sorry folks, but it blew away the digital! Even if this is by no means an "audiophile" recording (rather the opposite). Why is this? Why do I find myself "listening" to digital, while I become "immersed" in the analog sound? Don't know. Maybe, some conditioning is at work, I am used to playing LPs, but I don't think that is the whole story.
I should add, re: "blew away". This was the result using the Lyra Atlas cart with the Aesthetix Io phono preamp - costing much more than the Teac, so in those terms the playing field is not even in my system.
Mijostyn >I never evaluate music with the headphones- -  Me too. I like the staging and feeling of music better through my speakers. Using phones only for reference e g when recording from vinyl. Recently I’ve considered, maybe I should give headphones another chance, and have ordered a used Audioquest Nightowl, supposed to sound quite organic and "analog".

Orpheus10 and others,

I again seek input regarding preservation  ("archival") of music recorded prior to the hi res digital era.
Does playback (with or without digitization) of lp's made, say 40 years ago, from audio tape offer advantage over hi res digital transfers made today from those 40-year-old tapes ?

Is there better preservation of high frequency information on the lp's ?
Headphones are not for mixing, at least not ideal. They are for fine work, determining issues, etc.