In my case, I am upgrading all of my system to an “end state” leaving the speakers for last. Maybe an end state will never actually be achievable but with my Diablo 300 and it’s DAC module that together I adore the sound of, on my relatively modest B&W 803 D2’s, I think I have a chance. Currently upgrading to speaker wires that alone cost more than my speakers (Nordost Valhalla 2). Next I need to add a turntable (probably VPS Prime 21) for which my Diablo has a phono card.
THEN I plan to spring for speakers that match the rest of my system which already exerts a sonic character that I love on a variety of speakers. I could potentially look at B&W 802 D4’s (I auditioned the 802 D3’s with my Diablo originally). But a bit worried that the upper-mid-forward presentation of D3 and later B&W’s might not be for me. Sort of makes the bass feel lacking when it’s not actually the case. I want to like them, so transparent with abundant details with imaging so great it’s spooky. But the Diablo character is so clearly present still which is so good. Maybe I’d be fine with the more obvious mids; it’s not as if I dislike the sound. But expensive mistake if not!