Your "eureka" digital moment

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.