I personally find my SR325is, plenty comfy and I'm totally with jay. Sound is #1. Unless a can is a torture device (and I haven't really encountered any phones that are this way) it's fine by me. I did think it was interesting that in one of the recent promotional videos, the Grado family said that they've grown every single year since they started making headphones, and there seems to be constant stories about their success floating around. They make a good product for sure!
And I remember Mike Moffat of Schiit in an interview with Tyll saying something I thought was great: "Too many audiophiles nowadays sit around with their $100,000 systems, and you tell the guy 'I heard something in the highs that disturbs me' and its like you burned the guy's house down!' This little combo here (the schiit magni/modi stack) is just meant to be cheap fun. It's just fun, because that's what the hobby is about." or something along those lines. Truer words have seldom been spoken!