The MDR-1R wasn't at the first place in terms of sound quality because K550 has more neutral sound, wider soundstage and like you said faster. The MDR-1R is pretty good for both outdoor and indoor as it foes benefits from an amp. Overall, the MDR-1R sound FUN while the K550 sound "Serious" as in neutral really depends on what you like.
The K550 are actually suitable for outdoor unless AKG provide a case, a detachable code and a shorter cable but of corse, it's pretty weird to carry such big stuff while on the go.
Oh no I agree, its more so that the K550s met my expectations, where as the 1Rs exceeded mine. I would agree that they K550 was definitely technically superior. I would love to have the K550s, but I already have a pair of HD650s, and 325is, so its hard to justify them in my home rotation, being a broke college student and all. I think I'm going to take my tax return and fire&forget at the MDRs, though. I lost my Shure 530s( not so sure how this even happened..), and I've been wanted a new portable pair anyways. With that said.. do you know of any over-ear portables that have the sound of the Sonys with maybe a bit tighter bass, and maybe more neutral overall? I'm pretty set, but I'm never sure until I actually pull the trigger