Melos SHA Maestro (with the right tubes) + Grado RS-1
Singlepower Supra + Senn 650
Xin Supermacro v3 + Etymotic ER-4S
I own these combinations and feel like they synergize well. I have tried mixing them up, but these combos work best IMO.
Ditto re: EAR+ amp & Grado RS-1s -- I used to own that combo
Ditto re: KGSS (esp with Blackgates) & Stax Omega 2 -- have heard it and loved it
I've seen some great deals on used Dyn's on Agon, and I'm a huge fan of them. If you haven't heard a pair, I'd highly recommend taking a listen to some if there is a local dealer near you. I've often considered upgrading from my Audience 70s...but my money keeps disappearing.