Heya,
Mad Dog T50RP + Stax Pads (comes to just under $350 total).
All the dark goodness of the LCD2, excellent extension, good tight textured bass, and gorgeous mids. None of the brightness or imperfection enhancement of the T1 in regards to treble.
The HE-500 (the one I went with, over the LCD) is very bassy, darker than the HE-6, but not dark like the LCD/MadDog. I find it comfortable enough. It's not as comfortable as my Denons or Beyers. But I can wear it a few hours. It's a heavy headphone and all the pressure lands on the cups for me, the headband is a thin little leather strap with minimal cushion in it. I keep wanting to add some padding to the headband to make it very, very comfortable and put the weight of the cups on the band instead, but haven't gotten around to it because it's comfortable enough that I don't get bothered by it.
Alternative: you like the T1, so maybe just equalize the treble spikes down a touch so that it's a darker presentation, and you'll have what you're looking for without a cost.
Very best,