Analog or Digital and why?

"I was happy with digital too, when all I listened to was digital."

Well, I was unhappy with analog when all I listened to was analog (because that's all there was). I don't mean I was unhappy with the recording quality, per se. But I don't miss dealing with dust, needles, tone arms, or belts.  Not to mention scratched records, warped records, or trying to find what I wanted to play in a big crate of LPs, only to discover that some idiot (ahem) had put the record in the wrong jacket.  I'm done with all that. The one thing I missed, for a while, was the album art.  But now, services like Roon have caught up (to some extent) in presenting lyrics, artwork, and notes.

@jjss49 , interesting that you went with the analogy of food and particularly comfort food. Yes, there is no doubt that many people listen to old familiar music to avoid encountering anything new or challenging. As a former chef, I both understood and had little patience for such diners, because they were never going to understand my art, even as they enjoyed the food at their own level of perception. 
What I was getting at was the complete opposite. Returninng to known music opens up that which is strange, startling and unknown about it. The brain can focus on the details and structure that previously escaped attention. Thus, the long term relationship  versus one night stand metaphor Is an inversion. When I think back to my (too many) one night stands, the novelty was only skin deep, whereas my relationship with my wife of 20 plus years continues to reveal surprising features and things I didn’t know. 
Of course both are important and the human seeks novelty. I’d argue that our age hits that balance incorrectly, which is one reason that the early days of digital went for quantity over quality—an error that is very slowly being corrected in the main stream.

What I am driving at is less about Technical platform superiority (not a topic I find interesting in the least), and more about the art of music appreciation. In fact, I would put purchased high quality digital files in the same boat as vinyl—with replay equipment determining merits of each. 
Purchased collections are finite. For those of us who don’t possess collections of 100000 songs, the curated and limited collection has a greater potential to allow us that deeper form of musical appreciation. It isn’t automatic or even necessary—as the comfort food analogy makes clear—but from a behavioral perspective, a more limited collection stands a better chance of openIng more people to greater and more attentive listening than streaming. 
That’s my empirical assessment, and unless someone has data showing this is incorrect, a contrary opinion will be just that. I would be fascinated, however, to read if anyone has done a statistical analysis of how people listened to streamed versus purchased music. 

Records = headaches ,pops scratches,cleaning like space 
sonics can be Verygood but today you can get verygood digital
stsrting at under even $1k rhe Ares2 from a Denafrips R2R dac 
then better resolution and depth as you pay more .
metrum , dcs, MSB, Aqua , there are a lot of very analog sounding digital outthere one big thing a record st max can hold = to 12.5 bits of musical information on digital almost 21  true bitsMy brother has over a $20 k turn table setup and his $13 k DCS dac beats in in S/N ratio, dynamic range, Low bass  and musicality 
he said he just uses records for out of print and will transfer over to totally digital soon . I did that already I have non the time or patience.

Analog.

I've been buying records since the 70's, and have always concentrated on early/first pressings, and will upgrade to better condition or earlier pressings whenever I have the opportunity.

I've got over 3000 records, and whenever the "Latest/Greatest" digital gear comes out, I demo them with the best digital copy I can find to  an original/early pressing of the same recording.  Invariably I prefer the analog.

Same goes with "audiophile pressings".  I guess they're just fine if I can't locate an original, but they're usually not up to the original, especially if the remastering is done in the digital domain.

I have nothing really against digital.  It would be nice if the convenience of digital would come with sound closer to analog.  I listened to digital at work (headphones and an Onkyo DP-X1A) before covid and in the car.  Now that I'm working from home, I haven't used a digital source except in the car.

regarding analog - i cannot express how disappointed i am with the modern, high end LP reissues

such poor quality, such high prices

we analog lovers, past or present, are being punked

shameful