IME, what better (usually more expensive) dacs offer is a sense of realism. They do a much better job of transporting you to the venue. They're simply better at capturing the nuances, emotions, and the soul of the music. Once you hear that in your system, it's hard to go back to a lesser dac.
Other than that, when it comes to the usual suspects -- soundstage, imaging, detail retrieval, etc., most competent DACs have that covered. If that's what you're primarily listening for, then I agree it's hard to tell them apart ... especially, when you're doing quick A/Bs and wearing your analytical hat so to speak.
Of course, the rest of the chain, and very importantly the streamer, has to be revealing enough and synergistic with the dac to really hear what it's capable of.