When it comes to headphones, I think it would be simpler to take it as given that an entry level source, DAC and amp of adequate power will be able to drive your headphones transparently and move on to choosing your headphones... (or shaping them, as I do
)
If it's a matter of loudspeakers, invest in sound treatment at the first reflection points and then a flagship AV amp that has sophisticated loudspeaker calibration, eg Audyssey XT32.
My humble opinion is you're usually up a certain creek without a paddle if you're having to depend on the different sound "signatures" of different boutique source components to make or break your audio experience. If you need to change the sound of your music, change it for real (using DSP).