Okay, so I have a question:

How would the Pico DAC compare to the DAC in the UHA-6S (MKI or MKII)? How 'bout the CLAS -dB?

Am I going to be satisfied with the TH900s out of Shipsupt's old Gilmore Lite, or should I re-terminate to use it balanced with my upcoming balanced Dynahi?

Or, alternatively, will there be little to no difference out of my DAC2's HP out?

For full satisfaction, best to throw the G-lite in the trash and get a DNA Stratus or ECZD with the TH900. 

Okay, so I have a question:

How would the Pico DAC compare to the DAC in the UHA-6S (MKI or MKII)? How 'bout the CLAS -dB?

This is a good question.

I am using the Pico DAC now and I'm pretty happy with it for streaming at work to the 002.  I wonder how it would stack up in a close comparison with some of these, or even with the DragonFly or Meridian HI (High Impedance). 

It's the Apple connection with the CLAS stuff that still stands out to me.  The new  -dB seemed really attractive with added features.  I was seriously thinking of making the jump to the -dB and matching it up with a MKIII.  I'm hearing mixed reviews on the -dB vs. the original CLAS so I've held off.  In general I do find that I do prefer that CLAS in my chain vs. the iPod line out.  I don't notice it as much when I add it, but when I take it away I really miss it. 

One potential option...

The Philips L1 meets all your needs.  It folds and packs up easy, generally really nice construction, is over ear and comfortable, semi-open, easy to drive, and easy to listen to.  The phone cable makes them great if you have to make conference calls while on the road.  Good for movies in the hotel room.  I was living with these daily in the office for a while.  You'd want to get a listen to see what you think of the warm sound.  They don't do anything really bad, but they do lack some of the transparency, detail, etc... that you'd expect of a top end headphone (which it's not, so no need to compare it!).  Sound stage is marginally better than say the M-80 and HD-25.

I often stuff something in my suitcase when I travel, but always put them in some sort of case.  There are lots of options on e-bay etc... to fit almost any headphone, including Grados.  For example: http://www.ebay.co.uk/itm/Headphone-hard-case-for-Grado-iGrado-18cm-x-15cm-x-65cm-brand-new-high-quality-/150955699960?pt=UK_AudioVisualElectronics_HomeAudioHiFi_Headphones&hash=item2325a92ef8

My new hotel rig is the Stax 002.  I keep it boxed up in a small pelican case in the suit case with the earphones, amp, and DAC.