I went Tokyo Headphone festival 1996 today.
and I audition Senn HE1 + esoteric X05 disk player at headphone festival.
Not so impressed me at all.
I listen to CD Eiji Owe, Minnesota Orc. Stravinsky Fire Bird Suite(Reference Recording).
then I went my home and listened to same CD with SR-L700 + SRM007tA(maybe lesser amp than HE1) + Luxman DA-200(maybe lesser DAC than esoterics) combo.
HE1 sound fuller bass(+1) and not so impressed treble(slightly muddy). not so impressed.
L700 sound more musical and articulate treble and less bass.
I guess Headphone technology has already reached technological plateau.
First impressions often deceive. Maybe it takes more time to appreciate the HE1, but it's indeed surprising that you speak about muddy treble. Sennheiser claims they spent a lot of time on optimize the diaphragm thickness, tension and properties. Also, they spent so much effort on properly energize it... perhaps it is *them* who'd need some further optimizations to get that treble better, or could it be due to synergy with the other equipment?
I think even if there is a plateau, it won't last for long. Stax has made a few breakthroughs with the 009, what I would ask for is only a slight optimization or tuning towards the 007 or HE1000, that would result in a sound as close to perfect as I can imagine from a headphone.
On the other hand, when we compare the decades old SR-5 [Gold] with the current tech (007 and 009), they are not *that* far in musical enjoyment than they are in time, so you are right in a way, and actually they all are using similar diaphragms (OK, I don't know what diaphragm the 009 has, maybe not Mylar any more).
But I expect new diaphragm materials will emerge and that might be a jump.