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
The amp in the previous post would be a good buy. I have the M1 HPAP and it's a solid performer. It's only good for connecting source components though, the USB is not very good. 
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@bstatmeister or @mzkmxcv-
does the JDS Labs Atom Amp require a separate preamp for me to run it with my MHDT DAC? I’m hoping not, as it seems like many of the HP products combine components, such as amp/pre/dac. 

Im also wondering if there’s an amp/pre combo I should consider since I could easily unload my non-head-fi DAC for $600 or $700. As per usual, so many variables to consider...
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.