For me, the type of music, and the purpose of listening is also as important as the medium. You touch on this Armaegis, when you distiguish between attending a symphony and a rock/pop concert, which I completely agree with by the way.

There are times when I listen to speakers where I am only wanting background music (usually classical), but when I am at my desk and have bothered to align my lowly 5" near-fields, I am listening specifically for detail and stereo image.

With headphones, again, it depends on the music and what I am doing. The HD800 cannot be used for anything other than critical listening, focusing on a voice, etc. When its the HD600, I am able to slip into the music and let my mind whir on other topics. I love critically listening to classical music with the HD800, but when I listen to old country, bluegrass, etc, I find it too resolving, and I stop enjoying what I am hearing. Same with funk.

The weirdest thing (lately), is whenever I put on IEMs they help me tune out all distractions, including the music. When I really need to focus on something, I think the detail I get with UERM (combined with the void outside noise) overloads enough of my brain so that I can actually focus on just one thing. I know its there, and actually enjoy it a lot, but I don't can't think about it.

you're overthinking it mate

I used to be involved with choir, playing piano, attending the school band functions (which often times would have combined events with the choir classes), etc. when I was in middle and high school. Haven't been too involved since.

In those scenarios, I'd never really focus on the minute details, so to speak. Would get too swept up in the more emotional aspects of what was going on. When playing piano myself, while, yeah, I had to focus on the technical aspects of my playing, can't say I'd focus on things like, "How does this piano sound different than this piano?" or the subtle, damped thumps you'd hear when using the pedals, again, those minute details. Not that I wouldn't hear those things, but I'd get waaay to mentally involved in, uh, the musical aspect of the music. Things like letting the melody carry me away or really put as much emotion into my playing as possible. Same for singing. All those smaller aspects...they were just kind of there, but never anything I focused on or thought about. (Now, something being out of tune or sounding horrible...might as well scrape my nails on a chalkboard.)

When going to live events, it depends. Something like, say, and orchestra, again, I'd get really swept up in the emotion, the melody, the music...things like that. Never cared to think about things like how individual instruments sounded, their small characteristics, room characteristics (unless horrible and distracting), and so on.

Live events like concerts...well, that's a different story. Those are more just fun that anything else. Metal concerts, I'm not there for fidelity. It's a fucking metal concert. Though I DO get pissed off at how many venues sound like SHIT. Too much bass, horrible room acoustics, one guitar being louder than the other, drums overpowering everything, etc. Do I still enjoy myself? Sure. And when you find a venue that does sound good...man, that's a real treat. Actually, a lot of the heavier bands I listen to these days are very progressive. The type of band where I'd love to just sit down and listen. It's a real shame when those venues sound band. High school was the time for going ape shit during a metal concert, but my tastes were different then.

The funny thing is that I can go to a stupid loud metal show, not wear ear protection (though I usually do these days), and I do NOT get fatigued the same way I do when listening to headphones at a much lower volume. Sure, I'll get ringing in my ears and might have some level of fatigue, but it's completely different than what I get from headphones.

With speakers, that's when I start to notice small, subtle details and characteristics. Again, still mostly focused on the emotional side of the music that sweeps me away, but with a more critical listening aspect to it. It's sorta 75/25 with the 25 being critical listening.

The funny thing is, much like live venues, I can listen to speakers much louder than headphones with amps and DACs I'm not crazy about, and I still don't get the same sort of fatigue. I've listened to speakers that have slight midrange or treble issues that don't particular fatigue me. I might be bothered by the tone, but I'm not fatigued. (Yeah, I know, there are speakers that would fatigue me. I'd like to stay away, thanks. No HE560 equivalent of a speaker, please.)

Now, transition to headphones...those slight tone issues that wouldn't fatigue me on speakers all of a sudden become a huge problem for me on headphones, even at low listening levels. This is true of any genre, even something like acoustic or orchestrated music (particularly soft, mellow, or well recorded tracks are usually OK). Rock or metal, sure, those are the worst offenders. Having something like the HD650 paired with a NOS DAC and a warm, smooth tube amp (but not too flat with dynamics) is a godsend for me.

He adphone listening is more 50/50 in terms of "emotional" vs "critical" listening. I can just really dig deep into things with headphones, where as speakers are more likely to "move" me. The problem is the weird fatigue I get from headphones. It's an uphill battle for me, and I just have to accept what works for me, even if others can't relate. I'd guess guys like Anax would be driven up a wall listening to a headphone setup that works perfectly for me.

I'm sure some are wondering why I don't just use speakers all the time. Unfortunately, all of my rooms suck for speakers, and I'm waiting for my next house to dedicate a room to a good speaker rig. It's coming, eventually. Plus, the wife isn't always crazy about my music choices or my repetitive listening habits. On the other hand, there's something about headphones that captivate me, even if it's a real PITA getting something just perfect for my weirdo self.

Should also make note that I CANNOT do anything that requires much focus when listening to music, no matter speakers, headphones, genre, volume...Yeah, I can clean the house or do yard work, but those are mindless activities. Even trying to write a post in a thread is difficult for me with anything playing. Same for trying to read, say, a news article. I also get some form of weird mental overload at, say, a loud bar where as I don't get the same thing at concerts. Just thought I'd throw that in there in case something is related to the above.