I have pursued both for virtually all of my fifty years with visions of a high end system. Headphones are for the times I cannot listen to my main system.
It is true that the acoustics of the space are not a concern with a headphone system... all other aspects are the same. Matching, choosing the right sonic quality and ultimately they can be jaw dropping good. It took me decades to get there. But when I did, I couldn't believe how much of the high end audio experience could be delivered through headphones. I use Sennheiser 800 headphones which are have a very light touch and are open so you they are not at all fatiguing to wear for hours. The richness and depth of the bass is incredibly satisfying and the natural and musical sound is just spectacular. You can see my Woo / Ayre / Aurrender system under my UserID. It took years of effort and it was the investment in the Woo amp that completely transformed to sound... Takatsuki 300B tubes also contribute.
I can listen for hours.
