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

Thanks Greg!  I agree.  Keep them coming.  

 I suppose since I'm the OP that I should chime in. 

Vinyl did not always sound clearly better to me UNTIL I started moving up the chain with a better amp, pre-amp and cartridge.  And, the number one thing that opened the door to vinyl crushing digital was a great phono preamplifier.  I bought a Manley Chinook and I immediately noticed a holographic image that digital just couldn't deliver.  

Just about a year ago, I could A/B vinyl v. digital and I was a little bit apprehensive in setting up the audition because I wanted vinyl to win.  Well, now that I have a fairly decent cartridge (Dynavector 20xh/Ortofon 2M Black), a real phono preamplifier (Manley Chinook), and a decent integrated (Primaluna Dialogue Premium HP), I just KNOW that switching the selector over to digital on the integrated is going to leave me wanting more.  

I've had a turntable since I was a kid in the late 70s and was semi-serious as early as 1996 (I bought my first Rega then as a junior in college).  But while I always liked things about vinyl I didn't see it as necessarily superior.  I'm super happy to say that now I do see vinyl as better.  My bank account can attest to that.   All I want to do is spin black discs, and my Tidal account and DAC don't get weekly use.  

The holography, texture, realism, and--well--lack of flat, smeary, boringness to the sound make vinyl a clear winner.  I WISH vinyl wasn't better because I'd save money on music, record cleaning, cartridges, etc.  The maintenance and tinkering are kind of fun though.  

I'll say this.  I'd move from tube back to solid state amplification (both for main amp and phono) before I'd move from vinyl to digital.  

I will also say that my patience and curiosity to continue to experiment with digital has waned.  I have not tried many DACs.  I stopped after trying a Creek Sequel and a NAD Master Series M51 DAC--Sterreophile Class A product.

I'm open to the idea that I could keep trying DACs and I may eventually match the sound of vinyl.  But I question whether that can be done, whether it will be a long process, and whether I will enjoy doing it.  I coupled the Manley Chinook with a nice used Dynavector and got the holography, realism, and fatigue-free listening I wanted.  I'd rather buy more records and experiment with cartridges than be buying DACs left and right. 

If you live in Chicagoland and want to bring your killer DAC over and A/B vinyl versus digital over some drinks, let me know!  I'd enjoy it.

@jollytinker 

"I haven't spent more money on the digital side of the system because I just don't believe it will change the sound significantly enough to justify the outlay."

This is where I am at too.  I have an NAD Masters M51 DAC (Stereophile thought it was A list) and I can't get it to sound as good as my analog section either through Tidal's masters, through hi resolution downloaded files, or through CD to the DAC.  It does sound great though. Maybe the NAD is not the best, but if it's a Stereophile Class A I wonder how much more I'd need to spend and I'm not confident that it would get me to the land of Oz.