An epilogue:
The concept of the GR8s intrigued me, so I borrowed a guy's Shure IEMs at work. I think I can safely say I will never own a pair of IEMs! The sound is what it is, but they don't feel good in my ears, and quickly get gross.
On your advice I auditioned the Beyerdynamic DT770s (220Ω), AKG K271s and the Audio Technica ESW9A. The Beyers and ATs were thankfully available for A/B testing at my local Guitar Center, where the dude was extremely cool. The ATs I purchased from Adorama, who managed to take 7 days to deliver them the 120 miles to my house.
My source was iPhone through the CMOY; audition material was some early Pogues, Nina Simone, Shins, John Coltrane and some jazzy hip hop from an artist named Count Bass D.
The AKGs were by far the most open sounding and likely the most accurate. They were also the most comfortable headphones I've ever worn. The sound was nothing at all like the Grados, but I liked what I heard -- every piece of material I fed them was handled attractively with great detail. I feel that However, I found their look to be far too ostentatious -- they may be comfortable, but they're also huge and wide. If I worked in a studio, not an office, they'd have been the right choice.
The Beyers were quite comfortable, wide and detailed with all sources. But the reproduction wasn't always attractive. The Pogues track sounded especially cold and lifeless, likely because it was recorded that way and I'm used to hearing it spiced up and smoothed out. In fact, it wasn't until I got to the Count Bass D track that I was really impressed. These phones can handle some bass! I have since discovered that several of my DJ friends swear by these phones for their ability to track beats.
The Audio Technicas impressed me immediately with their opulent materials and classy executive look. And I discovered that I prefer the on-ear phone to the over ear phone. The over the ear phones had a little better isolation and required a higher volume to leak noise, but the ATs were good enough that they blocked out nearby conversations when played at low volume. They were not initially very comfortable, but over a week they loosened up dramatically. They aren't as wide as the AKGs but they have a well defined stage. Reproduction is certainly more Grado-like than the others, flavoring the audio in key bands. However, highs are so fast and accurate that they can be harsh! I've always disliked the way MP3 models cymbals and high hats, and the ATs turned that into hate. None of my lossless audition tracks sound bad, but some of the rips I made in college are so harsh it becomes fatiguing.
I have decided to stick with the ATs -- mainly because when I listen to them I don't constantly wish I were listening to the Grados instead!
Thanks all for your advice.