Your "eureka" digital moment

I got into digital in 86 or 87. Very conveniant but I never gave up on vinyl. Digital was ok but something did not "make sense" musically. Until 2001 when I bought a second hand meridian 508.24. Then digital made sense. No, not a perfect player (dynamics were polite) but oh what a listenable player. That was when I finally got digital. 
768e3cdc b761 4131 ab7d b47af0995626zavato
WAY back when I plugged my very first Tube component(Yaqin Buffer w/Mullard 6922)in between my CDP & SS Integrated amp.All of the sudden digital had everything vinyl did with none of the bad.
My digital "eurika" moment was when I got rid of it.  Prior to that it was high res digital.

For me, it was this Parasound, I think it was called a cpd1000 or something I bought for a hundred bucks...supremely listenable!  Very polite, but I could listen to jazz for hours on end!  Was very sad when the laser finally died.  But, the sound of that player still guides what I'm looking for from digital to this day.
My ’oh $hit’ moment came with my first pioneer CD changer in ’83...didn’t like it, but kept it and my TT and waited; there had to be some way to get better digital sound...everything sucked, really, but the upper mids and highs in particular...yuk. Fast forward to 2010. Stumbled into electronic noise reduction by way of Alan Maher Designs. Started off buying a $25 gizmo that seemed to help out a bit. One thing led to another and have kept buying more and more stuff from AMD steadily since then and am now in a position (albeit 5 years and about $10k later) in which I can use any digital player I would ever care to and they would all sound supremely analog. No need even for expensive wiring. All the problems there were with CD playback are now gone and it is no longer an issue for me. I have all of the convenience and none of the bad sound. Took a lot for me to get there really, but that’s where I am and that’s where I know I’ll stay from here on out. My "eureka" moment is every time I listen now. Ditched the inexpensive TT I had some time ago and, since about 3 or 4 years ago, have never looked back.
I thought I had always been missing something with digital based on everything I read about vinyl. I finally purchased a very nice $6000 analog front end and had my eurika moment. This was about 8 years ago. I realized my digital front end was better and never had to wonder again. The clicks, pops, surface noise drove me crazy! Underneath those snap, crackle and pops the music sounded no better. 
1986/87, Yamaha stack at the local mall stereo shop- still impresses me.
Vinyl guys will jump in saying snap,crackle & pop are due to improperly cleaned records & you need the $2500.00+ vac. cleaner to really hear vinyl at it's best,LOL!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
Well, I can chime in- I started this thread. Yes, I love vinyl, no, snap crackle and pop only works for cereal (but a clean record helps) and I bought my VPI cleaning machine second hand for $325
When I first played music from my modified 47 Labs Flatfish! I never thought digital could sound sooo good!
I think my eureka moment came when I discovered Spotify.  I already had a system I loved the sound of, which couldn't have been simpler - computer connected to integrated with built in dac running to speakers. So only 3 components including the computer, and only two cables, USB & speaker cables.   Realizing that for $10 per month I had instant access to 20 million songs through that simple system was my eureka - so much music and so few components required to bring it to life.  Simple + variety is a nice combination.
FYI folks I did clean the records! This was my real eureka moment  and a real experience. Can't I have it? Yes, a record cleaning machine was used. The noise is real and relative to CDs distracting. This is a simple reality of the medium relative to CDs. 
As much as the romance of vinyl appeals to me,the simplicity of my laptop with 40,000 songs wins the argument.
My "digital moment" came this past week after I replaced the two stock fuses in the ARC CD7se with the SR RED fuses. I thought the player was good before, but now ... WOW! Digital in my house has now gone from "convenience" to running serious competition with my vinyl rig. 

On the "snap, crackle and pop" ... I have thousands of LPs, both mono and stereo. Many are 50 years old and older and contain music that's not available on CD. I'll take a little tape hiss and a little noise in order to enjoy the music that's hidden in those grooves. And by the way, many of my records are just about silent ... even the mono recordings.
As soon as I switched from CD player to rip and stream via a good quality DAC only, about 7 years ago or so.
Mine was the same as Map's except I was already using a Benchmark DAC.  FLAC-to-JRiver-to-USB-to-Benchmark was vastly superior to CD-to-Wadia-to-Coax-to-Benchmark.
For me, the closest to such a moment came after I had loaded a significant part of my collection (4400+ CDs) on a music server--I had no idea how important it is to have the ease of browsing and accessing the collection that I now enjoy.  I listen primarily to digital media these days.  The sound of digital media is very good and enjoyable.  But, as someone who has both a nice digital and analogue setup, I know that vinyl, at its best, outshines digital--the music sounds more harmonically saturated (dense), the attack and decay of notes sounds more natural, small changes in dynamics are more readily apparent.  Good analogue tape is at yet higher level of performance. 

Agree with larryi. Being able to access and listen to my music library remotely when out of the house is an additional bonus. I use Plex application exclusively for that. In home, I use both Plex and older Logitech Squeeze devices still as well.
Never had the "eureka" digital moment. There has always been something aggravating about, some more some less.