I don't really keep any of my old IEMs :)
I take a deep breath, sell my IEM, and then buy a new one. I don't A/B them against other headphones... I just get a sense of whether I've made a mistake or not. For example, this is the second time in the past two months that I've owned the 334s. I tried a few other high-end IEMs and then decided the 334s gave me the best sound with the least compromises.
The pricing issue always comes up with any high-end headphone. We saw it 15 years ago when the HD600 ($300) was high end, we saw it when the UE10Pro ($1000) was high end, and we see it with the LCD3 ($2000) being the new high-end. There is little room in this hobby for second place. I look at the $1000 price tag and I know that Shure is releasing an IEM to compete with the best. They put me on notice. If they succeed, I'll watch the resale value of my 334s drop by hundreds of dollars. We'll put Shure on a pedestal and thank them for raising the bar 1 millimeter higher.
The price vs. demand curve for the best headphone does not follow any rule of economics. IEM audiophiles are a niche within a niche and they are very price indifferent. This would happen in any hobby.
Edited by utdeep - 6/11/13 at 8:35pm