Highest resolving and natural systems I've heard were multiples of $100k, practically that much on vinyl setup alone. Those systems and my aural memory of them has long been the reference for my home systems. IME not extremely difficult to get pretty high levels of resolution, transparency from digital, the issue is attaining the same level of natural timbre, timing, spaciousness that I've heard with the very best vinyl. At the level of vinyl I'm speaking of you're getting every bit and more of the resolution and transparency of digital, but you also get a certain feeling of relaxing into the music along with the extreme resolution/transparency. While digital is closing rapidly on this front, I still think some work needs to be done.
Another issue with determining a general sense of digital's potential is how highly variable streaming setups can be. Streaming noise floors and systematic induced jitter may hinder dac potentials. I fully expect with further innovations in streaming hardware and software, digital will continue to close the gap on the finest vinyl setups.
As for my own vinyl setup, I fullly expect I'll never reach the level of vinyl reproduction I'm talking about here, digital is the future for me.