Sorry, but after having owned two different pairs of the HD 380 Pro and using a pair of my friend's (to whom I recommended them), I haven't experienced any issues with comfort on the HD 380 Pro.
FYI monitor headphones were built with the intention of being flat and accurate as possible, and the term "monitor" does mean quite a lot. Whether this is a bad thing is up for the individual to decide. Audiophile has struck its own meaning as well.
As for the "questionable treble", it's a bit more upfront than other pairs of headphones you'd hear, but it's still natural and detailed. The HD 380 Pro headphones are high quality, and there isn't really much to argue with on that point because they just are, for their price. $150 isn't bad.
As for the Sennheiser Momentums being over-priced or over-valued, I have to disagree. They are absolutely amazing sounding headphones and they feel great too. They can hardly be called fashion headphones as they don't even look that great either. They just look...good.