Erik,
I do not listen to test tones or specs. I only use red book as digital source. There are few innovations in the digital conversion world that truly separate one product from another. Most use the same chip sets with various number of chips deployed and specific parts implemented in the circuit.
I have four four digital sources available in my main system. Three of them resemble one another in that they posses a more noticeable tell tail digital signature. The least desirable to my ears is the Oppo 105D circa 2015. Next up an early nineties Sony followed by a mid nineties tube dac from VAC. Then there is one that within that first 30 seconds of playback sounds that much more realistic to me that further comparison is pointless.
I also have an analog system while not state of the art is far above an entry level setup. If both the the analog and digital sound more similar than different this is a good thing in my experience.
However, the main goal for both is to sound like real music and convey the emotions and content to make me sit back and get lost in what's playing which is happening now as I type. Type a bit, stop and listen, then a few more words on the page.
An example of the 30 seconds test is track 2 of Holly Coles Don't Smoke in Bed. It's not a complex piece but revealing of digital nasties.
OBTW, I can afford more but what I have pleases me and that is all that I require. You're invited anytime for a listen.
