Just got back from the Montreal head-fi meet. It was basically perfect, we had all the big headphone players there (HE500, HE6, two HD800s, LCD2r1, LCD2r2, LCD3) and two summit-fi setups to audition them and other headphones from.
So here's my unadulterated impressions and comparison to my HE400s.
The ONLY headphone that was a straight upgrade from HE400s in every respect, was LCD3. Better timbre, better details, similar imaging, similar soundstage, amazing bass, and most important of all just a perfect treble in every respect.
LCD2r1 was pretty muffled, had a "cupped" sound. LCD2r2 is much more forward and aggressive than HE400s, but because of that has some bright treble sibilance and is in the end a bit less natural in timbre.
HE500s are more natural-sounding than HE400s, with a more rounded treble, but are a bit too bloomy in the mids, and the bass is not as satisfying as HE400 or LCD2/3s. This might be a full upgrade for some, but in terms of voicing I found it a tad boring.
HE6 is the ultimate "air" and "timbre" monster at the meet, basically a near-perfect compromise between HD800's detail/imaging level, and LCD3's timbre level. However it is still too bright, and I can't imagine listening to it for more than 2 hours. In comparison LCD3s have lesser air / imaging capabilities, but just sound smooth and easygoing whilst retaining all that great bass energy.
HD800s I hated...it lacked the bottom-end presence - the bass IS there, just not enough there for the whole sound to tie together and get grounded. There is a very interesting 3D holographic effect going on with sound physically coming from different directions almost, which was cool. The problematic treble even further reinforced the bass absence and with such a lack of balance I could not bring myself to listen to them for more than a minute. It might have had super details but the faults it has just overwhelmed them.
We had a HE6/LCD3/HD800 showdown near the end of the meet and the general consensus with myself and a few others is that HD800s have their ultimate strengths but are flawed in many sonic ways, meanwhile HE6 and LCD3 are both natural and near-perfect sounding, but have tradeoffs (brightness vs lack of air/imaging).
So in the end for my taste, unless I happen to pick up $4000 (LCD3 + good amp) on the road, I don't see an utter upgrade coming from my current setup except better upstream amp/DACs - HE400s scaled fantastically with better setups.
I auditioned lots of other headphones (LFF Paradox, AKG Q701, AudioTechnica AD900, HD800s, Denon D5000+full lawton mod) and compared them to the HE400s, if anyone wants my opinions on those I'd be glad to share it while my memory is still fresh.