LP made from a digital master recording...

My theory is this - if a digital recording is available in high res and you have a good DAC then the digital is preferable.

If it’s an analog recording and the LP was pressed in a purely analog manner (some lathes digitize the signal to do groove spacing) and you have an excellent Analog rig then that is preferable.

if no hi res is available, chances are the LP was cut from a 24 bit digital file and may sound better than a 44.1/16 download or CD or rip.

There are some who feel the LP compression pre conditions the signal and has sonic benefits regardless of digital or analog source.

It’s essentially a crap shoot and can vary by mastering and  release, and of course your system may be better at one vs the other source.

I sometimes buy cds and vinyl of the same album. It's often pretty close if the cd is not too compressed. Although I am a vinyl guy, I agree that it's not worth the effort if the sound is virtually indistinguishable from the cd. But sometimes, the LP is not as compressed as the cd or mastered differently ----and then there is a big difference. The only problem is knowing in advance whether you are wasting your money.

It’s essentially a crap shoot

You don’t know the half of it! Everything you mentioned and more can be done to perfection, and still only one in a hundred copies somehow against all odds delivers the sublime sonic perfection records are truly capable of. Only the lucky (smart crazed fanatical) few with White Hot Stampers know what I’m talking about. The rest of you can talk all you want about hi rez this, digital that. Its frankly great the way things are with hardly anyone knowing. Between the lack of facilities, expertise, and now even raw materials its hard enough to keep up with demand as it is. Which you notice, no such problem with digital. Dreck we got coming out our ears. Quality, never had that problem. So its really good people don’t know. Crap shoot. That’s what it is. Records suck. Go digital! Hi rez! Heh.

Great question.

Looking forward to reading some explanations and preferences. I think its purely a subjective call, but lets see the technical explanations for whatever is "better"

Yes, the euphoric qualities of vinyl still pervade the experience. Depending on the recording sometimes it is better sometimes not. Vinyl is always noisier so on very quiet recordings digital has an advantage. Older analog recordings, anything before 1980 I tend to buy the vinyl unless I know for a fact the digital is better. David Bowie's first three albums were digitally remastered, an absolutely amazing job so I got the high res digitals of those. Newer digital recordings I tend to get hi res versions unless it is music I really want and only the CD is available then I will buy the vinyl if it is available. 
I think every audiophile should have at least a few vinyl/digital duplicates.
It is fun to sync them and switch back and forth. Sometimes it is surprising how much alike they sound and often dragging a rock through a trench sounds better even if the music was recorded digitally. One caveat, better is not necessarily more accurate.