I participated in a ADC shootout with a 1/2" master. All was done at 24 bit, then 16 bit. There was a clear winner in the converters.
After it was done, the engineer played the 1/2" master straight through, no converters. It was not a question of noise, dynamic range, etc. It was a question of clarity, depth, detail, warmth, and all those other fuzzy words to describe ultimate audio. My jaw literally dropped. It had so much more life and truly sounded like the band was in the next room. This of course was with a grammy nominated engineer as well.
So I know what tech specs say, but I also know what my ears tell me. And technically there should be little difference in the 16 bit file to the analoge version, but not always. I will say that it does take a good engineer, good musicianship, and great equipment to make such music to tell the difference. It also takes better trained ears to tell the difference. I doubt my wife could tell, and I doubt a badly recorded track I could tell. JMO.
And yes, different masters can make a difference. Although I do remember a similar unscientific test a friend and I did with Dave Brubeck's Time Out. There are several versions and we compared a CD, to a newer 180 vinyl, to the new SACD. There was little difference in the SACD to the vinyl, but the CD was clearly from a different master and was hard to tell. So therefore, I cannot definitively say that SACD is equal to vinyl. We all know vinyl has it's own issues with mono bass below 140Hz, channel separation, RIAA curves, quality of equipment, etc. But yes, there are differences in masters.