Analog or Digital and why?

Digital all the way now. Analog will be dinosaurs in a few decades, maybe even less.

Best digital today is as good as and in many ways better than analog. Noise floor, dynamic range and ease of use alone makes it a winner.

Almost all the recent analog you think you are listening to, is recorded initially all in digital anyway.

I do love turntables & vinyl but not because they sound better but because they LOOK better & cooler :-)  At least I am being real with myself.

sometimes i want discover new music, music that comes recommended from various avenues in the genres i enjoy (and some other genres occasionally too!)

sometimes i want the comfort and enjoyment of listening to old chestnuts i love

when i have found music i really enjoy, it make it a ’favorite’ on the streaming source and will listen repeatedly/often

if i really love the music, i may pursue finding it in different media such as in LP form, just to have it and be able to hear it from a different source

imo the dating/one night stand vs marriage analogy mentioned earlier is misplaced and misguided, although the whole post raised some interesting points

better analogy is sometimes we go to new, well reviewed, recommended restaurants, sometimes we go to old favorites to eat our go-to items for comfort and consistencyn- reality is, enjoying food and dining, we do both - though obviously in varying proportions depending on preferences

Analog for recordings made before 1981, digital for after.

I’ll take issue with one thing the OP said-  “A modest system can be an easy 20 grand”

a modest vinyl front end is far less than $20,000. 
I’d argue that a pretty credible vinyl front end can be put together for $2,000

I travel full time in my motor home and I shudder to think what the equivalent weight of my 2,900 digital (FLAC) albums would be in vinyl form; 1s and 0s don’t weigh much! Not to mention the impossible physical storage!  Plus I rarely listen to an album all the way through and more often queue up several shuffled albums.