mcqueene,
New to the forum, just investigating purchasing the Image phones. At least for comfort comparisons, and taking into account that I may have small ear canals, I owned a pair of Shure E530's for a year. I travel all the time and no matter which foams, or gels I used, after about an hour my ears were killing me. I bought the Bose QuietComforts; great sound and unbeatable comfort, but when you travel for a living, way too bulky to carry all the time.
As far as sound quality, I can't imagine anything better than the Shure's with the three drivers. The Bose didn't sound any better to me; but I just couldn't get past the pain of the Shure's so I sold them a couple of months ago and have been looking for something else and it looks like I may take the plunge for the Image.
I will write a comparison between the Image and Shure 530's when I decide to purchase the Image pair.