Best Headphone system under $1000???


Hi all,
I've been a 2 channel audiophile for 30+ years, and I'm ready to liquidate the big system and simplify.
I'm interested in finding a really nice set of headphones and a headphone amp, to pair with my DAC and MacBook based Tidal streaming source.

Interested in staying within the $1000 range (or under) for headphones and a dedicated headphone amp/preamp.
As far as tastes go, I prefer a "musical sound" to the more hyper detailed hifi/neutral sound. I enjoy jazz, funk and R&B, classic rock, and some classical, so I'm hoping for a headphone system that is slightly warm and has good soundstaging.

For reference, my big system has Vandersteen 2CE Sig 2s, Odyssey Kismet amp, and a nice 6SN7 tube preamp from JE Labs. I like the full, colorful, dynamic sound of this rig and hope I can replicate it in a headphone set up. 

Any recommendations would be very much appreciated!
Thanks!
Lincoln
lincnabby
If you want dac built in to amp (all in one), likely nothing better for the money than the massdrop THX AAA 789. I think it's right around 500 bucks, but from what I understand it is a lightning quick amp that makes for superb Dynamics.

Otherwise, I would probably get a Schiit modi (DAC) 99 bucks, to go with the JDS Atom (amp) also 99 bucks. No preamp needed since we are talking about headphones not normal 2 channel stereo.
I have older 2CEs and an Odyssey Khartago. PM me if you're putting your system up for sale! (" For reference, my big system has Vandersteen 2CE Sig 2s, Odyssey Kismet amp"). The Kismet intrigues me!

As for headphones, I love my Sennheiser 650s, and the Schitt headphone amps are wonderful. To do a lot better I think you'd have to spend at least 2X as much.
I made the switch to headphones a year ago and haven't looked back. The musical signature of a good headphone system is that you enveloped by sound. Traditional speaker systems are characterized as the listener is sitting in the first rows, or the orchestra seats, etc. With a a good headphone set-up you are is sitting in the middle of the performers themselves. I listen to jazz and classical. My headphones are Massdrop HD-6xx. ($200) My amp is Woo Audio WA6 1st gen. I use Sylvania VT231 (6SN7) as driver tubes. Lots of air and prat. Good 
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Expect to pay around $500 for a used WA6 1st gen. (The newer 2nd gen. will not accept 6SN7's even with the necessary adapters. But you may be fine anyway.) You will need around $200 plus, for the adapters and tube upgrades. One nice thing about the well reviewed WA6 is that it will work with both low & high impedance headphones.
Thank you for the info @umn 
I will find it hard to not live with that 6sn7 sound. 
I’m enjoying the Focal Elex right now with my tube based MHDT DAC, and a temporary solution with an old Yamaha receiver as I await a JDS Labs Atom HP amp. I also have Senn HD6xx cans. 

I prefer the Elex on this non-ideal system, but still would like more of the warmth and soundstage of tubes. I’ll update once the Atom arrives.