If you're going to go the Stax route with a dedicated electrostatic Energizer then you'll really only need a streaming DAC for it. The Matrix Audio X Sabre Pro, Brooklyn Bridge, Auralic Altair or Aries, PS Audio DSD, dCS Bartok are all examples of streaming DACs that would pair with the energizer in ascending cost.
Of course the setup would blow away your budget, not be compact, and would leak a lot of noise... so essentially not meet any of your initial requirements. This setup would, however, provide you with some of the best sound available. I've heard the 009s out of a Blue Hawaii out of a Schiit Yggdrasil and that was one of the top setups I've ever heard.
Top hit your original list of requirements I would recommend the Focal Stelia closed back headphones with the Matrix Audio Element X as a Roon capable streaming headphone system that won't leak much sound, be compact in size, and fit near your $5k budget.
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- Dan
Headphone rig: Gustard X16, Topping A90, Hifiman HE6se, Audeze LCD2
2-Channel setup: Okto Research DAC8 Stereo, Bryston 4Bł, Philharmonic Audio BMR Towers, Dual PSA S152 subs
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