For the most part, they do sound the same, in my opinion.
That said, I HAVE heard clear, repeatable differences even with "bit perfect" output. For example, there's a track on a very well-recorded Celtic music album (I'd have to find it again) where there's a certain tenor note that CLEARLY distorts when played through iTunes (every time) but is rendered perfectly via Audirvana. And, yes, I confirmed both programs were set for bit perfect (i.e., no processing), the Audio MIDI settings were correct for playback from iTunes, etc.
I also hear clear differences between Foobar (for example) and Roon (or Audirvana or ... ). I think there's more going on than meets the eye, and I don't like it, frankly
being mostly a "bits is bits" kind of guy usually.