Most HD-800 buyers will be able to afford to keep their other headphones. Sennheiser is trying to capture a different market segment here - people who can afford a $1,400 headphone don't need to worry about unloading a $300 one.
The only hope is that Sennheiser will release the HD-680, updating the 600/650 and discontinuing those. If that happens, you might be able to grab a $150 HD-600, like when the HD-580 was discontinued.
This is an interesting gamble for Sennheiser. Around $1,500, the market shifts. The traditional selling point for headphones is that you get more sound for less money. I'm still trying to rationalize a pair, which might change after hearing them. I thought the HD-800 would have a MSRP around $1,000 (D7000, DX1000 and GS-1000 territory) with a street of $700-$800. But at nearly twice that, they run close to a used pair of quality loudspeakers. Some used speakers around $1,500 that interest me are the Magnepan 1.6QR, Klipsch LaScala, Quad ESL-57, and Quad ESL-63. That money would also come close to buying a set of drivers for Linkwitz Orion loudspeakers, which I'm thinking about building. Can the HD-800 really hang with the ESL-57? The ESL-57 is an unqualified classic and the other four aren't far behind. And could headphones really make a run at an Orion?
Another part of the gamble is what competitors will do. AKG is a rival and still has the very, very capable K-1000 within reach. If the HD-800 sells in any quantity, the K-1000 could go back into production and be priced $500 less. Grado could roll out a successor to the HP-1000 and Beyerdynamic is capable of great things. Their vastly underappreciated DT48 is as detailed as anything I've ever heard - something along those lines but more consumer friendly would be a contender.
This should be interesting.