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
Mijostyn, you don't need a fortune or a perfect room for critical listening. Differences in source material are typically more evident with headphones and a good headphone amp.  $3-4K in that area would be more "revealing" than just about anything with speakers in a room < $50-100K
audio2design, I think in relation to most systems you are probably right except for the evaluation of very deep bass. Apparently you have not looked at my system. What I have is essentially very large electrostatic headphones except the perspective of the soundstage is correct. Headphones can be a good reference for tonal balance. I have Grado Ref2 headphones. The system sounds just like the headphones from a tonal perspective. I never evaluate music with the headphones and I would think mixing/mastering recordings by headphones would be a big no no. They have special systems set up for this. The perspective of the music is wrong and setting up a proper stage would be more difficult. I greatly prefer the stage I get on my system and the visceral sensations you get with live music. This is all missing on headphones.  But, I am no recording engineer so if I am wrong please tell me. I just know what I am looking for in my own system.
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".