Turntable got absolutely crushed by CD

And then there is the phono amp...

I'm skeptical when I hear a cartridge is aligned perfectly in all parameters.  I read this post as azimuth parallel to the record, mid VTF,  VTA is admittedly off and, since no break-in is mentioned, a used - maybe very used - lower end cart.  The main bearing could have a flat spot increasing the noise floor.  On top of that VPI regularly sends out a table with the P2S way off, meaning the supplied jig will produce improper overhang.  The quality of the integral phono pre is suspect too.
Yes, digital is much easier and takes less devotion.  You're in the trenches with analog.

"Had everything dialed in.......... All good." You forgot to say, "Trust me". No mention of stylus condition(if purchased used). Too many variables! ie: The C-200L preamp was released over 30 years ago(1984). There’s an excellent chance, that the electolytics in it’s phono section, have dried up. All it takes is one bad cap, to ruin/degrade sound from any component.

MC cartridges need a good step-up transformer (SUT) for best sound! High-gain phono stages won't do! I know this from 40 + years of using MC cartridges! In fact, the best active head amp I heard was a Levinson JC-1 clone. It was very, very good with the 103. But my Verion (Cotter) P transformer was even better! Lower noise floor and more dynamic sounding! 

At this point I feel like I should give up on analogue playback and invest further in digital.

Your call. You can get your vinyl sounding closer to your digital, if that is your objective.

As long as you understand that Vinyl is a total setup game based on vibrations and resonances. It is only (somewhat) plug and play for that person that is happy and content with the outcome of the first setup. No need or desire for further tweaking.

Since you are making comparisons to your digital, and finding the digital better, it's up to you to decide if you want to pursue this. If you do, I recommend keeping your current setup and focus on the tweaking of your current setup. Just changing the turntable feet and stand components will dramatically change the sound. As will using a higher still  VTA;  since you state that the Bass is more with vinyl (it shouldn't be)  Just remember that when you change the JMW tonearm VTA, it is NOT "on the fly" you will need to readjust the other set up parameters. Once tweaked out if your setup is still lacking compared to digital, then consider changing out components, if you desire.  My 2 cents.   

With that, as ones experience grows on how to refine the setup (usually through trial and error ) to manipulate and manage these vibrations and resonances, your vinyl setup can continue to be improved. How far you go down the rabbit hole depends on your state of Audiophilia Nervosa at any given time. 

So good luck and have fun since you are dealing with the audio hobby aspect, discussing how "Gears" sound, and not how really great that album is, no mater what medium is used to play it.

fwiw . I have also found a bass recording emphasis on Sarah's LP's.   Surfacing has some really low tones that can test out how much your house, floor, walls, TT components, (wife) ..... vibrate.

 8^0


https://www.youtube.com/watch?v=GYC9N4fVd6g