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What is your opinion for the price limit on headphones for listening to digitally compressed music from online streaming like Spotify ("extreme quality") on an IPhone? Is there a real difference between this or AH-D7200 over something less than half the price (AH-MM400)? Or with Sennheiser's HD800 vs. HD599? At what point does headphone amp make a difference?
I'd say that if you listen to a lot of compressed or streaming music, you won't want a headphone with a lot of treble extension, as that's where the compression is most audible and extending it will make the artifacts only stand out more. And I wouldn't worry about chasing the highest spec sheet when buying a DAC or other digital source. I'd also be more inclined to look at high quality wireless options for convenience (if that's your thing) because they won't excel at hi-res and you won't need them to do so.
My portable phones are the Bowers & Wilkins P7 Wireless.
I currently own both TH-X00 and HD800 as my top favorite headphones. I do have HD580 somewhere in my garage that I just don't want to go back to. Everyone knows this :^)
320k is sufficient, although CD quality is more optimal. I can't even tell the difference between native 11.2MHz DSD vs PCM, but people with golden ears might be able to. DSD and 24/192 files are ridiculously large btw. Just enjoy your music rather than format!
Headphone amp difference is more of a controversial topic with a lot of subjective debates, but I personally think they don't affect the sound as much as headphones. There are sonic differences but it's subtle compared to swapping headphones.
Note: I spent over 1K on amps/DACs just to minimize possible bottleneck.
Also there are plenty of good sounding headphones that cost much less, for example DT880 and K712. I'll be getting D7200 after it is released.
edit: excuse my wrong tag.
Headphone amps are "necessary" in only two cases (soley my opinion):
1) Super sensitive, low impedance where your current source present an impedance mismatch (some phones/portables and Shure 846 or other multi-ba iem)
2)Very low sensitivity (Hifiman old gen)
Beyond that it's just preference and source compatibility. I find an amp tends help the bass be a tad bit more impactful and the treble smooths out a little. An amp can help "get the most" out of your headphones or provide greater connectivity options but I've never met a headphone that was transformed by an amp that didn't meet one of the previously mentioned criteria.