Wow, talk about a blast from the past - I remember this thread from a couple of years ago.
I've been around head-fi long enough (I was a lurker since the beginning of this forum) to know that the legends aren't always that easy to recognize when they're new. Some - sure, the Orpheus was always a dream system and no one ever had anything bad to say about it, but as to where the R10, Qualia, and especially the K1000 would fall in the pantheon of greats was not as easy to recognize because of all the mixed opinions and the initial post-FOTM sales in the forums and on the 'gon. I remember seeing K1000s being sold used rather cheap before production was discontinued. Just like Michael Jackson, there was a big surge of renewed interest after the announcement of the K1000's death.
I also wonder where some of today's newest phones will fall once the dust settles and production inevitably ceases: the Audeze LCD-2, the JH13/18 Pros (and DSP / Amp), the SR-007 Mk II and even the D7000, T1 and HD800. (Those last few are probably the most predictable of the bunch in terms of long term value because of high volume production).
Earlier in thread, there were some questions of whether things were fundamentally different now compared to the 90s. I think so, and in two significant ways. I think the amount of interest in headphones and head-fi has grown tremendously, and internationally. The number of members and volume of posts in this forum (and in the for sale sub-forums) and the last few Can Jams is pretty convincing evidence to support that. The market is larger. And secondly, the interest in, and quality of IEMs has grown tremendously - the question is whether that is enough to cut into the sales of high-end full sized headphones.
Full circle back to the topic - where is Sony in all this (and arguably Audio-Technica as well). They have built neither a new flagship full-size headphone nor a high end IEM in recent years. I would have thought that they would respond to the HD800 and T1, not to mention the explosion of high-end IEMs. They will probably just suddenly appear some day, a true successor to the R10s - I can't wait.