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.
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.