Without reading through your entire post, I can tell you that with the right equipment, there is positively, absolutely, no difference in the sound of vinyl being played on your TT, and vinyl that has been ripped to your PC that is being played back.
Some years ago, this debate was raging, and what I just stated was concluded. But you have to have the right equipment.
Not favoring analog or digital, I listened to the PC people and the digital people, as well as "Stereophile", and I got it right. Everyday I listen to my vinyl that has been ripped to PC, with the confidence that it is no difference from listening to my TT through my analog rig.
As a matter of fact, when I upgrade my cartridge, or anything else, I have to do the recording process all over if I want to enjoy the upgrade.
I hope this answers your question.