Interesting thread. In my experience, you can always make improvements on the front end of the system--the line or phono level sources, and yes, even interconnects sometimes--and hear those improvements pretty clearly on whatever speakers you have. But the reverse is not always true.
Once the low level signal stuff is tight, anything you improve on the speaker/high-level signal end may well result in dramatic, easily heard improvements.
And regarding digital, I've been unhappy in various ways w/digital since the '80s, and only recently really got happier with it, thanks to multibit digital DACs, specifically NOS (non-oversampling) multibit. This has been a real game-changer, to the point that I no longer even think about my digital source (just enjoy it).
Once the low level signal stuff is tight, anything you improve on the speaker/high-level signal end may well result in dramatic, easily heard improvements.
And regarding digital, I've been unhappy in various ways w/digital since the '80s, and only recently really got happier with it, thanks to multibit digital DACs, specifically NOS (non-oversampling) multibit. This has been a real game-changer, to the point that I no longer even think about my digital source (just enjoy it).