The Road Not Taken indeed. I disagree with you on your second point, but not specifically with iTunes files, but when it comes to less than "super high resolution digital audio files." Lately my favourite listening has been done with music such NPR Tiny Desk concerts on Youtube. A well-made recording beats all in my experience, even if it is played back from an AAC file.
Lately, for something different, I have been using Vox for playback. It seems to have come quite a long way for a simple player.
Yes, I would indeed agree that the production quality trumps all; perhaps I should be more careful to properly narrow the context of my opinions.
My main point was that I was trying to lower anxieties over 'which' DAC to purchase. There are many that are quite good, so waiting around for the 'best' DAC to appear is just delaying catching the wave of accelerating 'audiophile' enjoyment. What that is, Beats me? (Hey, those blinking blue lights have made it Kool to be geek for the Millennia & CupCake Gens).
To validate your point, however, have you ever listened to acoustician Evelyne Glennie's performance on ted-dot-com over YouTube? I would be fascinated listening to that through a rubber garden hose standing in the rain during a T-storm. Check it out!
I am thrilled that you are enjoying such a multi-input auditory experience. "There is more magic in sound than sight, when done right," to risk self-quoting.