Never really thought I'd say this, but I'm in the family now. Went out to Fry's tonight and picked up some Sennheiser HD 598's for $150. I was able to test them at a Tiger Direct store and man were they comfortable! The sound definitely won me over as well, but comfort has always been first and foremost for me. If I don't want to wear them, what difference does it make how good they sound? On top of that, my Christmas present this year is going to be Dan's Audio GD unit.
The Oppo 105 is still tops on my list. Even though this headphone rig is taking about $400 from that purchase, I think in the long run its going to be a good investment. My main rig is not conducive of anything but listening to music, so at least this headphone rig will keep me glued to my desk while working on lesson plans or grading papers next semester.