Hey pwnified, I hope it performs nicely for you!  I don't know if I mentioned this, but I put the JFET inside the guitar (1/4") plug, and it fits pretty easily.  I had to wear glasses for the job though.  
 
Yeah, I don't see any obvious reason the iRig may have crosstalk, nor any obvious difference from my design, so I really do need to test mine for that, when, as you, I get a free moment.  Peavey claims 
"AmpKit Link is a powered device with circuitry that virtually eliminates feedback."
  I don't know specifically what this means, but it's intriguing.  Maybe a cancellation circuit?
jkevinwolfe, it sounds like you're doing the right experiments to minimize headphone-to-mic bleed.  Best case (with the large cans), would you say it's near zero?  That gives us a reference point for the quality of the isolation inherent to the earbud jack itself.