[silverlight]

So I'm in audio nirvana with my desktop setup and am really happy with it (electrostatic, HE90's playing out of a Woo WES maxxed w/ nos tubes, source is a Amarra 4 DAC / heavily tweaked headless mac mini with linear psu and lots of power cleaning).  Itching to get some nice quality audio while on the road.  Would plan on using uncompressed files with (1) ipod touch dock output, or (2) ipad USB output to portable DAC.  Based on the system above, I like tube sound (slightly warm side of neutral, don't love overly analytical sound that gets fatiguing), I'm not focused on excessive bass but enough for a full sound, like great soundstage and accurate extension w/ HF's. Spend most of my time listening to singer-songwriter, light rock, contemporary folk rock, acoustic, guitar, and occasionally classical, choral.  My only experience with IEM's is with some shure se430's a while back and I currently have Monster turbine pro copper headphones but I find them to be less transparent and fairly rolled-off in the highs (admittedly this is relative to a pretty high standard in my desktop setup, so not a judgment on them in any way).
 
I don't have a particular budget in mind, rather the priority is portability and sound quality (and a good fit that's not fatiguing, hence thinking about customs).  Have been looking at the JH13's or JH16's (with a Whiplash TWag re-cable), TTVJ slim amp (w/dac), pico slim, pico amp/dac, etc.  Totally open to suggestions on headphones and amp's / dac's.  Also, curious if the usb output on the iPad with an external DAC is significantly better than using the analog dock output with a good 3rd party dock wire (i.e., ALO Audio's).
 
Thanks in advance for help, and my wallet is at your mercy