Maybe, but we need a constant to compare, and vinyl seems the target. Not enough folk have Reel to Reel to use that. I wonder if the old 44.1 can ever level to vinyl, is there enough resolution on the file to do that? If the studio master is in digital but super high res, then in theory a digital file at near the original bit depth should beat vinyl, if the DAC is up to it. Or is the RIAA system doing something to the sound to make our ears prefer that presentation? RIAA was designed for tubes, so it makes sense it will sound better on tube amps. Is digital just too revealing in the treble region, and loosing density, weight and timbre in the midrange? I have no idea, just saying out loud what I have heard on a good vinyl rig.
A super test would be, play an original recording as reel to reel in the same system v vinyl copy v digital copy (at the highest bit depth possible) then see how it compares. If vinyl is different to the reel to reel, what is different about it. Is it the RIAA that is making its sound more pleasing to the ear?