I regret getting a DT880 years ago, instead of the HD600. Everyone seemed to love the Senn, but I had a stupid need to be different...gosh, all that time wasted trying to find the perfect amp for it, when I was never really satisfied with the fundamental sound (is this even the right term?).
In general though, I have to admit I've spent more time and money on audio than I really should. I just don't know and listen to stuff the way that you guys do. Should have stayed in mid-fi land and been done with it.