Your "setup"

>minidisc
damn, haven't seen that crap in decades

i never liked that AAC compression, mang

Headphones: Bose Quiet Comfort 15s
Speakers: Yamaha HS8 monitors
mainly through my car speakers

Martin Logan Motion 10 Front speakers
Martin Logan Motion 6 Center channel
Noresco 5870 omnipolar (surrounds)
Yamaha HTR 6050 receiver
Peavey 8.5C power amp (for subs)
2 big ugly home built sub cabinets with old school Rockford 15" subs

oh shit dude i got motion 15s myself

They've got a heil of a tweeter.

Yamaha HS8 through a steinberg UR22 MK2

Headphones don't compare. Although when I use headphones its mainly My M50's or xb900

M50x and Foobar on both windows and Android. Most of my music came from the archive, but I try to pay Bandcamp artists when I like it enough.

My Vinyl system
Rega RP1 table with Ortofon 2M Red Cart
Pioneer SP BS22LR speakers
Sony GX800ES receiver
D-Box David 300 subwoofer

How much can you all attest to the difference of high quality speakers, headphones, etc?
I listen to music through cheap, shitty Coloud headphones and I think this is good, how much of a of a difference do you all actually hear comparatively? It feels incomprehensible to me