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Once I started listening, I was expecting a lot more "drama" between the headphones and amps I've selected - ortho vs closed, solid state vs tubed. The differences are certainly there, but with the HE-500/D700 getting such raves along with the Schiit/Burson, I thought for certain the winners in my comparison and final choices would be dramatically obvious. So far, they are not. This is not to say I am underwhelmed by the quality of the gear, but more so the differences between the gear. And yes, I had unrealistic expectations due to reading so many forums. Listening for oneself is paramount.
Like you, I've often been caught up in "analysis paralysis" by reading the various opinions of pieces of gear. Most of this information tends to be posted by regular, longer-term posters here on this site and not necessarily an individual who just signed up yesterday. However, when one makes the leap and they buy gear where the company doesn't have a return policy, then they suffer because they have to factor in some depreciation / loss into the price when the list their item for sale. After 2, 3, or 4 cycles of wash, rinse, repeat ... one often starts to wonder why are they making so many decisions with the great gear purchases that are not living up to their expectations. This can be quite frustrating. I've been there, done that.
So, essentially, I've taken a somwhat differnet path. Granted, my path or my solution that has made me the happiest isn't necessarily the most portable. However, it's what brings a big smile to my face as opposed to having to live with product "x" even though it has one or two shortcomings that we have to learn to live with. In that case, I've found that a good integrated amplifier or receiver from a few years back, and affixed with speaker taps tends to work the best for me. The best sound is presented and very few, if any, shortcomings are experienced. The only downside is the 20 - 24 Lbs. of gear. Now, it's not only the issue with DACs and amps that may not live up to one's expectations. I can also be the main source, too. While I've locked in on and believe that the iPod Video / 5 / Classic is one of the best bargain players out there, it still suffers from short-comings. One can't really by-pass the DAC that's in the unit, but they can bypass the built-in amp via the use of a LOD cable. Ideally, I'd love to pass the DAC, if possible, to see what truly the player is made of. Then again, the Wolfson DACs that were used are not that bad.
In the end, I think most "portable" gear is best left for driving smaller headphones or in ear monitors. For the HifiMAN headphones, the full sized integrated amps are my power of preference.