On most players, volume is controlled digitally. This means you have to find the volume at which your player behaves like a lineout (no digital attenuation of the signal). For Sony A8xx players it's full volume.
Amping the player with a D2... I don't know if it's a good idea: the Sony is considered a warmish player, and the D2 amp is warm as well. You'll make overall sound signature more opaque. This will be great for Etys, not so much for IEMs with subdued highs, or bassy. I wouldn't do this for Westone ES2.
My understanding is that you might be better served by an iQube (550$!), SR71, AE-2 or Minibox E+ (180$).