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

It proved to me that the differences between analog and digital aren't solely at the front end. Synergy of the system is what makes one better
than the other.

Precisely!

Correction: Stan, not Steve, I am getting old!! @whart I did not check All the responders, only hardliners and those who find digital more pleasing to their ears. If Rega P1 beats Linn Akurate is one thing, if Esoteric beats VPI is totally different story. Overcompressed crap sold as "progressive" nowadays (sorry, Steven Wilson is just a lucky exception) sounds crappy no matter what. Van Der Graaf Generator "Live" from the olden times sounds as horrible thru LP as CD. Symphonic Dances on RR sounds totally Awesome on HDCD, but makes me jump when I am not too lazy to warm up my Armageddon.. All things being equal, vinyl always wins to my ears, but the convenience of Hi-Rez or CDs rule! 

Hello, I own 3 turntables that are setup in my system now along with 3 fantastic phonostages. I have one excellent digital source. Even though digital is extremely good, vinyl does edge it out when it comes to which sounds more LIFELIKE and REAL. I could be very happy with only listening to digital for the rest of my life  but when vinyl is setup correctly, it is superior. But vinyl is also more of a pain in the ass setting it up and changing records. 

1973-1987 - bought tapes and vinyl.  Made many mixed tapes on Maxell chrome dioxide tapes.
1987 - impulse bought Cure double cd and had no CD player.  Sounded better than my cheap turntable.  Was cheaper and portable in car.
1987- 2015 bought thousands of CDs.  Climaxed as music rip marathon, dac dabbling, software purchases thought it was better than cd.
2015 - impulse bought Beatles reissues on sale and had no turntable.
2015 - bought used rig with used cart and new wall shelf and jaw still hits the ground.  Have relaxed about one off imperfections in vinyl reproduction since live concerts are as imperfect as they are great.  I would exchange my 5000 cds in the basement for 500 records.  Off the digital upgrade fever train, so can back fill my records now.  All good.

Eggs ackley! Digital by and large is an analytical medium, it begs to be examined and analyzed like a monkey examines a skull. Whereas analog is not analytical. It just is. Tape and vinyl are natural mediums. They breathe.