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very wise words ...
the funniest thing is that the e17 + hd600 combo makes my lossless feel like a there's group of people inside my head playing their instruments perfectly but having no "connection" with each other - the detail is incredible, but no soul
but play any mp3 and you feel like you're in a concert with them - the bass is boomy in a nice way, the treble distorted in a nice way, the vocals is projected through an imperfect analogue microphone (every detail coded in defective compression is brought out in a nice summative way - but of course the candidly nice effect won't last i don't think)
weird
Now, when you say the bass is boomy and the treble is distorted like in a live performance, you're probably getting too much EQ effects somewhere. Do you have the E17's sound processing on? Granted, my experience with Alpine's MediaXpander typically makes 256kbps files sound like that, but the boomy bass and distorted treble are only a reality in live music if you're standing too close to the stage or any of the speakers. If you were, say, 30th row dead center, the sound crew was competent enough to mind sound quality as well as pure db's or at least the venue wasn't bad enough acoustically to force too many compromises, it shouldn't sound like that. Even if you make concessions for the fact that modern music isn't necessarily performed in places where Mozart or Wagner prefer to perform, what you're basically recreating in that set-up are the imperfections of modern music performances, as opposed to hearing them as neatly as in a studio. Imagine acoustic live sessions, or even with amps, but you have the drummer and then he's get the amps from teh other instruments and vocals placed in the right spots in front of him - that's basically the general sense of what studio albums (or live session albums) have to sound like.
Now, as for lossless being too detailed but not necessarily great for listening, has a lot to do with :
1) Frequency response - too much treble detail with too little/too flat lower midrange, commonly known as "warmth," that makes voices and instruments have enough "body" and reverb to sound natural.
2) PRAT - Pace, rhythm, attack and timing. This has a lot to do with beats, and basically when you listen to a song (barring those that are too melody-centric, like arias), that basically make you tap your feet or snap your fingers to the music. You can look this up in Hi-Fi glossaries for a more detailed look into the whole thing and the individual attributes, but jsut to give you an idea, try listening to Feist's "One Evening" (lossless) on different gear. On one set-up I had before the beat was just there, while in another the notes overlapped and were trying to compete with the vocals, in my preferred systems the beats initially sound a little loud but very separate from the rest, but immediately begins to fade quickly and is nearly gone by the time the next note comes in. Now, as with any sound characteristics, any system is to be taken as a whole, but apart from the speakers/headphones, the power of the amp relative to the requirements of the speaker/headphones and its slew rate, as well as the slew rate and frequency response of the source (I'm assuming here the amp is and should be transparent enough), determine all of this.
Perhaps the overall sound of your system is due to the more analytical DAC of the E17 workign with an amp that, for the HD650 at least, is inadequate. Just because it has enough power to get loud enough does not mean it has the current and slew rate to match; for one thing, it runs basically off a battery and/or 5v USB, no monster toroidal transformer surrounded by capacitors (as in the overbuilt PSUs on the amps on AMBLabs' site, or most Meier amps), etc. It's not necessarily a bad amp, it was just designed differently - for one, it can fit in your pocket, vs how much desk space a Concerto or Beta22 will need. If you had an IE8 instead of an HD650, chances are you might not be craving for a tube amp, or any upgrade for that matter. Still, did you try listening to classical music on the E17 and HD650? In a good recording this kind of reproduction can be an asset since you might probably be able to pick out where each section of the orchestra is.
In any case what we can draw from your description and assessment is that the Valhalla may be the best choice for you to try out. If you live in the North America, Schiit has a 30-day guarantee, so it's really worth trying it out.