I could write a long paraghraph, but I will just say this: Focal Elex, Verum 1, Denon 5k (there’s also the ESP95X which I have yet to unpack so I can’t comment on it) don’t need a crazy amp and I will gladly match them up with the Timeless or similarly priced IEMs any time of day. Same for other headphones though, especially things like the 6XX, 560S which are pretty overrated imo.
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I think the background noise reduction provided by IEMs and the potential impact on dynamic range could be a factor in your (OP’s) perception.
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I’d agree, somewhat more forgiving headphones when it comes to amps, they don’t need one, but they sure benefit from having a nice one (also not to ignore the dac, since if the dac can’t do it properly, neither can the rest of the downstream components/chain)
The 560s wasn’t really as special as some made it out to be for me, although I think the 6 series senns can be incredible with the right pairing, but it’s a lot more picky amp wise than a lot of the aforementioned. But still I see many not really a fan of it, it’s a specific sound for a specific taste
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Open HP’s = a hot, sweaty and heavy way to fail at replicating speakers…Closed back HP’s = even hotter and heavier way to fail at replicating IEM’s…Simples.
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IEMs = a failure at both replicating speakers and headphones. I personally wouldn’t take an approach like this because I don’t really think headphone designers are really trying to replicate speakers or iems, or iems replicating headphones or speakers, and definitely not speakers trying to replicate headphones or iems lol. All 3 provide distinctly different experiences from each other, imo they figured out long ago that trying to replicate the experience of another format/medium wasn’t really that fruitful and it was better to focus on what the format they chose did best at. If you are going to go about making an iem, might as well focus on taking advantage of what in ears do best rather than trying to turn it into something it’s not, same goes with other formats. At least that’s just been my experience with the 3
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I liked that 
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Very wise thoughts. You should not try to do one thing with another!
Doesn’t help that I have an old 650 which probably sounds different than the 6XX… I accidentally wrote 6XX cause I’ve absorbed the notion that both should sound the same but they probably don’t…
They don’t sound exactly the same but they are close enough to where I think it’s safe to use them somewhat interchangeably, they are more similar than not
But this is what makes us human.
Many have asked what differentiates humans from other animals. Some point to a “soul” or “spirit”, but thus far, we have been unable to scientifically observe or measure this aspect, so I will dodge the metaphysical question as not able to be compared at this time.
However, others have tried to point to intelligence as the difference. This argument is continuing to decay and crumble as we learn how very intelligent many of our cousins in the animal kingdom actually are. Others try to use our language as a point of differentiation. However, again, the vocalizations of many of the great apes as well as those of marine mammals are more and more beginning to be revealed as extremely complex, communicating not just simple intents, but emotional and coordinative logistical information, and even regional dialects are being revealed. The more we learn, the more the language argument is crumbling as well. Finally, as a last ditch effort, some will point to tool use and/ or manufacture as being what makes us different. However, this argument too is beginning to crumble as we have observed some apes not only using sticks and rocks, but using sticks and rocks on one another to improve the intended function, and then keeping a well made tool for future use.
Only the human, however, can deliberately choose the wrong tool for the job.
Only a human would be laying under an American made car, with a set of imperial sized sockets and wrenches, and discover that the bolt he needs to remove is metric in size. Now, this human knows he has a set of metric wrenches 15’ away at his toolbox, but heck, it’s only one bolt, so he grabs the pliers that are right next to him and tries to use them to remove this bolt. Only a human will skin all four knuckles on his right hand when the pliers slip, because he was too lazy to climb out from under the car and walk the 15’ to get the correct tool.
Only a human can deliberately choose the wrong tool for the job. This is what makes us unique in the animal kingdom.
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Yes, only man makes the same mistake twice.
I might’ve made this specific mistake a few more than twice 
That’s right. In fact, the strange thing is that even very intelligent people make the same mistake two, three, four or more times. That’s how we differed from animals - they don’t!
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Any thoughts on the Edition X V2 vs other Hifimans like Arya/Ananda?
I will add that budget IEM’s likely sound better than budget headphones, but competition gets tougher as the budget goes up.
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My personal take is that (open back) headphones sound more natural and have a wider soundstage at every price point.
However, IEMs have better technicalities like resolution and instrument separation and general clarity especially in the lower and mid price points until about $1000 where you’ve got something like the Focal Clear.
And my controversial opinion is that IEMs are better than closed-back headphones at all price points.
So to summarize, my thoughts are you either want to spend a small fortune to get a really nice open-back headphone which will have the best timbre and excellent technicalities but will also be much more limited in its use cases or get some IEMs.
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