FWIW to be honest nothing beats the listening experience to tell you if something sounds good or not. You can study digital audio infinitum via internet articles and forums but ultimately listening with your own ears is really the only way to pick your way through the technical worm holes created by all things digital. This is what i have done and not taken too much interest in the technicalities although I have read a great deal but arguing one system, piece of kit or method is better than another really means nothing until you have first hand experience.
I have been lucky and heard some great stuff and the evolution of really good digital audio but it reminds me of Digital photography, you know how it went 2mp camera then 4mp, 20mp. Then it was all about sensors etc finally we ended up with some amazing digital photographic equipment and thats just in a phone!
Similarly I have been following digital systems as they have evolved and some are just about there in my opinion of course. The learning curve has been steep, after all vinyl took about 60 years or more to get to a really great level of audio quality so I am not surprised digital has taken some time to mature and the techies have unravelled what is important and what needed to be fixed.
I am in the same boat as the OP and would like to put a system together that would be as good as or a match to my vinyl and hopefully soon I will but it certainly will not involve a CDP and will be File based probably with ROON running the software.