Interesting thread. Being new to Headfi and still on the verge of choosing amps and cans, I have the tendency to compare music gear to camera gear. In order to understand price vs value of these expensive music gears, I tried to find a small (and probably senseless) analogy between them and my photography gear.
MP3 players = Camera body. No matter the form and different options from multiple technology, it still serves the same purpose.
Headgear = Camera lenses. No matter the source/body, the headgear/lens can make or break the shot/listening experience. In a lot of cases, the headgear/lens could either enhance or depreciate the intended shot/media.
Amps = Support system. Sometimes you can get away without using an amp/tripod. There are work-arounds. But higher impedance headgear/long focal lengths or non-stabilized or simply slow lenses, will demand the use of amps/tripods. Others, could simply benefit from it.
EQ = Darkroom/Editing software. Despite the areas where the headgear/lenses might come short of service, eaqualizing/editing would help enhance or improve the listening experience/photograph. But they could only go so far. A crappy sound/photo is still a crappy sound/photo.
In my opinion, music and photography gear can relate to each other when it comes to prive vs value/use. Photography gear is just as expensive if you really splurge into it. Lenses and Bodies and Tripods are relatively strong in some aspects and weak at some. But one can make due with what one can afford. Although desiring for more or better gear, you can still enjoy listening to music/taking photographs with what you have.
But to me, there's a difference when it comes to productivity. In my case, it's easier to get a bit more financial compensation from my camera, than from my (future) music gear. Although, one of the main reasons why I end up here in Headfi, is that while taking photographs, music is a huge muse. The music I currently listen to, could make such a big impact with my shots.
To answer the OP, my piggy bank meant for an expensive support system, will be sacrificed in the name of headgear.