If its for Audio, it matters. If its for digital domain video, not so much.
Experience with live instruments being played (not necessarily amplified instruments) helps a little. May be a little easier with video (what DOES a train running into a bus sound like?). Most entertaining works there.
I guess it comes down to your taste and what you like - or have come to believe is most acceptable.
Best extremes I've heard and liked for obviously VERY different reasons are Quad Electrostatics on one end and Khorns on the other (Audio).
Most of all the rest fall towards the middle if made before MP3 algorithms.
Best compromise I have heard between the Quads and Khorns are VMPS IIa/r circa 1987 (like a Border Collie / Mastiff mix kinda). Got the VMPS's now but am thinking of going back to horns, maybe.
Older stuff IS better for Audio. I remain hopeful.
Video - anything that is dynamic, images, and has a KA sub.
Then again that's just my opinion and I could be wrong
My 16 year old Samsung SACD disc player (DVD-HD841) has the same DAC as my much newer (2017) Panasonic, and Sony (2019).GEES!
It is now 11 years + and things are not a LOT different (or better?).
Old link (above) brought me back here.
STILL have the VMPSs ... I do like the newer / better DACs now ... NEED to find correctly recorded music w/o compression, etal.
Class A amps still sounds the best (if you can find them new).
Tubes? Still sounds good (with the 'fur').
WHAT (really) has changed materially outside of listening judgement and continued Volume Wars in these 11 years?
Maybe the better DACs?