Headphones: Hifiman Sundara, Grado SR60 (detachable cable modded)

DAC: iFi Zen DAC (v1)

IEMs: CCA CRA

I'm quite satisfied with the setup, though I sometimes wish I had over-ears for on the go because my ears get fatigued from IEMs pretty frequently, especially during cold weather.

I'm also entertaining the thought of an upgrade from the CRAs or a complimentary TWS IEM.

And I'd like an open-back that's suited a bit better to gaming. But other than that I can't really complain. Not really expecting to replace the other equipment soon.

I haven't had a huge amount of experience but:

Headphones - Superlux HD 681 EVO (sibilant to some but in my opinion it has a fun V-shape that isn't too fatiguing)

IEMs - CCA CRA (once again fun V-shape but surprising amount of detail and technicalities for the price)