Thanks to all for the replies! A few follow up questions and clarifications.
From what I've read, it seems like the Valhalla is THE Schiit amp for the 650 in this range. That's good to know, but I have the Lyr 2 already, with no plans to switch it. Also, for what its worth, I'm using 74 Voskhod Rocket SWGP Silver Shields from rb. So, I've got good tubes, although I haven't yet stepped up to the over $250 range.
So, should I be looking at a different headphone for the Lyr 2? The other pair I thought about is the AKG Kxx from Massdrop.
The boxes I'm trying to tick are:
Super comfortable to wear all day
Relatively mellow ( i love grados, but this is not the use case for them )
great sounding
good looking enough not to be embarrassing
The reason I keep coming back to the Senns is that I feel like they'll scale with gear. They've been around forever, with easily replaceable parts and high build quality.
Still, Liu said "If that was your only headphone, I might pick something else in that range."
What would you guys recommend?