why were you disappointed? there are a lot of good options in the mid-range portable headphones. if you can be more detailed w/ what you're looking for maybe I can throw out a few recs. theres the v-moda m100 (more bass), sennheiser momentums (similar sound as 1r, but more technical & better build materials), akg k550s (more neutral, but big & not really portable). the ue600 has recently dropped down to $190. ultrasone pro 900 has a lotta fans. the mad dog is not really portable, but has really highly reviewed SQ.
For the MDR-1R, I was mainly impressed w/ the comfort. I haven't had another pair of portable over-ear headphones as comfy as those.
Yes the comfort is good , in terms of comfort all the Sony headphones I have owned (V6,zx700 and ma900s) excel , the thing about the 1r is their Sibilance , now I can't talk to much as I didn't spend a lot of time but ....... I can vouch the HM5s best it , yes in comfort too IMO