I wonder if the differences are in the area of noise, detail extraction and ease/flow or naturalness. I've only heard a few analog systems rival the ultra low noise of digital. But I've also only heard a few digital systems approach the liquid naturalness of great analog. Resolution can be great with both as can dynamics.
I respect the advantages each format has, but I always return to the comfort of analog. I'm sure it is nothing more than my personal/subjective bias or preference, and the cost and effort involved with starting a digital collection from scratch.
I would also humbly suggest that moving up a tier in analog with a different table and some isolation will improve things on that front. I am fairly certain your arm and cartridge are at the top level, though I have not heard the combination.
It would be very interesting to take the Vivaldi stack over to Albert's or Babybear's system to compare with their analog, or conversely, listen to one of their turntables in your system. It intrigues me that I think all three of your tables are Direct Drive - GP Monoco, Technics SP10 III, and Dobins The Beat.
Don't hold back on providing more details about the sound. Very curious.