Can I get recommendations for headphones up to around the $2000+ range?
My sound taste is about the same you'd find in a tube amp review: emotionally involving, endlessly musical, smooth, and just makes you want to listen to the music rather than analyze technical merits of your rig. Something that can make anything, even bad recordings, sound musically endearing. Accuracy and all that is not something I focus on too much. I know some people can be "It's so accurate, etc. that you just can't stop listening" as their definition of musical, but for me its more in the traditional sense, if that makes any sense.
The DAC I'll be using is a MHDT Stockholm Balanced (about the same as a MHDT Havana), which is a NOS tube DAC. The amp I'm so far interested in the most is a DNA Stratus. Both of these components reflect my taste in sound if that helps with seeing what I like.
Quick background on past rigs:
Bijou + Valab NOS DAC + HD650 was far and away my favorite since it had everything I described above. Extremely lush, romantic sound that made you want to listen to it endlessly. My honest desire is to replicate this sound except on a higher tier of sound.
Audeze LCD2 + Violectric V200 (using its built in USB DAC) was a resounding MEH. In a technical sense it blew away the above setup for soundstage, dynamics, extension, and all that, but it had very little emotional involvement or musicality for me. I'd put it on and WANT to like it since it was so damn expensive, but I'd just take it off maybe just a couple songs later. There was absolutely nothing that I could really say that was bad about the sound... it just didn't captivate me on a emotional level, I guess.