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 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 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) 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.
emrofsemanonm audio2design, atmasphere and others
Hard to disagree with any of your statements.
Regarding phase shift and other 'distortions' more prevalent in vinyl than digital recording, electro-mechanical lathing/playback (with RIAA equalization) seems of central importance.
Regarding potential frequency response with vinyl, again no argument.
This frequency response....higher frequency I would argue better preserved by playback (with or without subsequent digitalization) of vinyl pressings contemporaneous with the original recording than by 'master tapes' of those recordings, because of time-dependent degradation of the tapes. 

I set up with both high rez digital, and 30 ips analog tape. Stereo X/Y pair fed to microphone preamps. The signal from the preamp was split, one side went to A to D, the other side to the analog tape inputs. I could feed any of the three signals to the headphone amp and 2 pairs of Senn HD800s. The listener could select between the live mic feed, the signal coming off the tape, or the output from the A to D/ D to A converter. Most were shocked they could not hear a difference between the live feed and the signal off the tape, but could hear a difference between the live mic feed and the output from the converter.

I find this statement suspect and can only assume a mistake in the setup. For far too many hours of my life, I have heard what has come off the microphones, what has come off digital and what has come off tape. If you have a good quality digital system, the direct feed and digital feeds are indistinguishable, assuming levels are set the same. Tape on the other hand, especially if you know what to listen for, absolutely will have a distinctive sound, even, since I would assume this is portable, 30ips - 1/2" - 2 track. Even with 30ips, in what I assume is a very quiet environment, you would notice, with headphones, subtle tape hiss not evident on the digital feed. I am giving you the benefit of the doubt that at 30ips you were not using noise reduction, since that has a distinctive sound all on its own. If these results occurred, I would go with, poor digital chain, or digital chain levels not matched.

On the master clock front, studios use a master clock for synchronization, not for ultimate quality. Transmitting that clock around the studio and decoding it will impart more jitter than an internal good quality clock. In a studio where you can have multiple ADC, and digital processors, it is advantageous if not essential to have the sampling synchronized. That would apply even more so if you need to have sample accurate synchronization with video. Good studio ADC will have better specs using their own internal clocks than with the master clock generated in the studio. As studios modernize and move to IP (ethernet) networks, master clock domains get smaller and smaller being limited to only local equipment. IEEE1588 over Ethernet provides enough synchronization accuracy for most usages.

For consumer DACs, an external master clock has no practical purpose. It is relatively easy, and inexpensive to generate an internal clock in a DAC, and that will not be susceptible to noise on an interface to an external clock. That also does not handcuff the consumer DAC to a set of arbitrary external clock frequencies that may not be ideal for that equipment.
For kicks last night I decided to do something I had not done before. I recorded my Mo Fi 45 rpm copy of Santana's 1st record to the hard drive then played both back  synchronized as close as possible. After matching volume I spend the better part of 30 minutes trying to tell the difference between the two switching by remote from my recliner. There were times when I thought the treble may be a little recessed on the digital side but I could not make up my mind if it was real or not. I probably should have had my wife do the switching. 
@mijostyn   Its funny how much better a master digital file is than one that's been exposed to DSP!

It seems that the latest posts are from technicians or engineers, as opposed to "high end" music lovers.

The reason I specified "high end" is because most of the qualities pertaining to high end audio gear can not be measured; as a matter of "fact", after the engineers finish with Audio Research amps, they give them to audiophiles who don't even know Ohms law for final tuning based on their educated ears.

I have earned a living as an electronics technician, and I am a devotee of high end audio equipment. We begin where specifications end; that is in the subconscious audio realm in regard to the subjective evaluation of the music.

Presently, I'm listening to a new noiseless record that has me in a state of quiet euphoria. Were I to compare it to a CD, I already know the difference; "some of the emotional component would be missing"; we call that "musicality". The only meter qualified to measure such a quality resides in the mind, which is located somewhere in the brain.

Like many of the finer things in life, this love for high end analog is left for the connoisseurs of such things to enjoy, while those with less sophisticated taste look on.