You're comparing apples to oranges in a sense, because headphones are a different kind of experience. I've owned reasonably high end 2 channel and surround systems in the past, but where I'm living now I can't really play a system like that the way I would want to, so I sold the gear and went all-in for headphones. Bought Focal Utophias, am driving them at the moment with an RME ADI-2 FS DAC/amp combo. I'm shopping like crazy for a dedicated headphone amp, but like most of us, have to rely or forums and reviews, so it's confusing. I would advise that you think about the sound signature you prefer in your speaker system and read reviews etc. in that light. Headphones are a much more intimate listening experience, so keep that in mind.
Headphones vs full range speakers
I've never had any really high end headphones. I had like a $500 pair of Seinhauser earbuds for a while. I thought they sounded really good even pushing off a phone. Question is who has gone from listening to speakers for your main listening pleasure to headphones or vice versa. Can get something like the top of the line Focal Utopia headphones while pricey they are in line with "mid grade" speakers.
I don't entertain often at all and the wife does not listen anymore. Just started thinking why not simplify and get some kick butt headphones.