When and how did you, if at all, realize vinyl is better?

If they put caffeine in the vinyl I might come back to the fold:)

If I want caffeinated vinyl I just go to starbux...

But seriously, I've been building a system for the past few years, piece by piece, trying to understand what "good sound" is, and how the different parts of a system effect the outcome. I've tried to be neutral about tubes vs solid state and analog vs digital. In the end i'm a tinkerer, not an ideologue, so it doesn't really matter to me which side wins out. Or so I like to believe :)

Anyway 4 years later I have a system built around an SET amp (Art Audio Jota) with an analog front end (modded VPI Aries 1) that has just come into its own with the addition of a Doshi Alaap phono stage. On the digital side I have a Baetis server running into a Chord Hugo DAC fed by a fancy Revelation Audio S/PDIF cable. I'd say they're roughly comparable on the audio hierarchy (?), though I've put way more time (and enjoyment) into the analog side (and money!). But the digital side sits largely dormant. The spouse recently looked at it and said "that shelf is for the defunct stuff."

So why does it end up that way? I like the digital well enough, but there's just something very different about it. Like @effischer  I don't know how to define it, and like @dentdog it just happens naturally as I'm listening. I gravitate to the vinyl and focus in; I 'enjoy' the digital while i'm doing other stuff, but it doesn't grab me. High res files help, but only so much. The best I can say is that it's like the difference between the reproduction of a famous painting and the experience of seeing the real thing. They ain't the same.

I think @gregkohanmim may have a point - the analogy in the method of production of the sound (physical object creating vibrations, rather than a software algorithm) may be the key. Yes we humans are very smart, but sometimes we claim victory before we've really got it right. I'm sure digital will some day (maybe soon) eclipse the sound potential of analog playback. But it'll be a good while before a $4 sound file sounds anything like a good $4 used LP! and for me that ends up making a huge difference.

"If they put caffeine in the vinyl I might come back to the fold:) "

Dave I somehow sense, based on your comments on this site over the years, that you seem in a pertetual conundrum over many things audio. Alas! you’re not alone, it is the bane of being an audiophile as we all well know. Whatever the medium the bottom line is, enjoy!

I've realized that the premise is not necessarily true. I’ve listened to lots of vinyl for decades and now use a CD player as my only source. I believe you can assemble (craft) an audio playback system so CDs will sound just as good or better than vinyl. Each step of the way, while improving (striving for a certain preferred sound) my current system piece by piece, iteratively, its only source was digital. End game: CDs sound terrific on my current system. I think often times people who believe vinyl sounds better are judging based on playback on a system which was not purposely crafted for a digital source.

Rockadanny, I for one would emphatically disagree with that premise!
My system over the past 15 years was changed, upgraded, focused on digital sound including multiple turnover of digital components to try to achieve a less fatiguing presentation of music.

I can only say that my recent focus on vinyl playback has eliminated any ambiguity as to which I prefer. It is as it has always been as the two are different mediums. To me it's not even debatable. Maybe because of my age and growing up in the golden age of audio.  I  believe that the relatively recent  renaissance of vinyl playback is a connection to the emotional aspects of musical playback which is the heart of the matter. It seems many younger listeners, contributing to this renaissance also recognize this as well. What is going on here? Is this a  nostalgia trip or is there something deeper happening? 

To me is is quite clear in the here and now that the main advantage of digital playback, for the most part, is convenience. I have had more than the last 30 years to compare,  no ambiguity on my part, vinyl still reigns supreme in musical engagement. Having said that I completely respect the opinions of those that disagree, whatever floats your boat.