I feel I can answer this set of questions, but only this one, as it is of general nature and not specifically about HD800. I'm still on HD650.
Yes, it is indeed much harder to find the ideal sound through headphones than through speakers. I think the major reason it that most records were mixed using studio monitors, not headphones.
Headphones, even the best ones, have very uneven and model-dependent frequency response compared to high-end speakers, due to natural physical limitations, for instance headphone-to-head-cavity resonances. Full-size headphones are also mono-transducer designs (save for some exotics that didn't take off in marketplace), which doesn't help at all with intermodulation distortion. And to top it off, reproducing surround sound is very challenging with headphones, and surround sound adds lots of naturalness to speaker-based systems IMHO.
I believe one can
approach the sound of a high-end two-speaker system using sound processing in the digital domain. First and foremost, this includes equalization, which counteracts the most egregious resonance peaks and valleys. This also includes crossovers, room simulators, exciters, and potentially other sound effects that modify the headphones transfer function to make it more like the one of a pair of typical studio monitors, for which the recordings were originally optimized.
I realize that this school of thought is not the most popular on this forum
Yet what to do? I measured the frequency response differences between some very highly respected headphones, supposedly rather accurate, on my head, and on some 1/3 octave bands in my hearing range the differences reached 9db! If left unequalized, there is just no way in hell either of them was going to sound accurate on all kinds of music. Compare that to the ridiculous flatness of my speaker system, which goes +-0.5 db across my whole hearing range (well, used to go, until I added a 4 db subwoofer bump at 72 Hz, as I'm a bass-head apparently
As an added benefit, my spending on this hobby declined once I proved to myself that I can equalize HD650 and DT770 to sound virtually identical for my ears (HD650 still sounds somewhat better, due to lower distortions). By extension, I believe I could equalize HD650 to sound very much like HD800 if I wanted (once again, HD800 is likely to sound somewhat better, due to more advanced mechanical construction). More importantly, you can make virtually any higher-end headphones to sound like anything you personally like! I now invest more in software and fast multi-core computers than in headphones.
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For you people that started out with a very good sounding speaker based sound system first prior to headphones, do you find it harder to find the ideal sound through headphones?
Do you feel it is harder to dial in the sound that you are looking for in headphone based setup since the sound is more intimate to your ears? Or does your headphone based experience exceed any speaker based system you have ever heard?