I totally understand you have experience with tube gear with guitar amps and inexpensive tube gear back in the day. However, the sonic characteristics you seek would seem to possibly be best served with some sort of tube in your chain. Whether that's tube in the preamp, part of the DAC stage, or amplifier. And there's a big difference in tube gear when you go up price tiers. Just food for thought do what you think is best.
Best advice for headphones would be to try is Meze Empyrean and Audeze, whichever you think suits you (LCD-X probably my favorite headphones because of the very realistic and natural sounding mid range). They just have a musicality to them with great bass extension. Otherwise some sennheiser 6xx with some super good front end gear (probably with a tube somewhere in there) would fit your preferences. As long as you also have the ability to EQ them (this is probably the most important thing I have said in this rant) - this goes for any pair of headphones. Can take your rig from ok to outstanding. Best of luck in your journey

