Does anyone have a digital system that is as involving as their analogue front end?

@audio-b-dog yes, I think you are right that, not surprisingly, if you want digital playback that is as engaging as your $25k investment in analog you will need to substantially upgrade your streamer/DAC.  And when you are ready to upgrade, my recommendation is that you look into R2R DACs, whether cheaper ones like Holo Cyan2, Denafrips or Gustard;  or even better, mid-priced ones like the LTA Aero. There was a recent thread on here with a bunch of good suggestions under $5k.   (And maybe give  @mitch2 ‘s 6 DAC comparison thread on here for some additional info and other great ideas, albeit at higher price points.  I’m currently trying out the new Mystique  Z quantum DAC from mojo audio and it is excellent and has the convenience of no tubes.)

I’ve found that Delta sigma DACs with ESS chips like the one in your Moon have a hard time sounding as musical as even moderately priced R2Rs. The streamer is important too, as you started your thread with, and if you want a streamer/DaC in one box , @audphile1 has given you his very well considered recommendation.  If you’re looking for separates, to allow for flexibility in upgrades, the Aurender N200 is a very fine place to start.  (If you find a deal on a used one, maybe even consider the N20.) I don’t see a used N20 or N200 at TMR at the moment, but they frequently have them and they offer a 30-day trial with a small restocking fee.  So that is one less risky way to test the equipment out in your room with your preamp and amp. 

It is an "apple/oranges" kind of thing. 

I am finding no matter what the source/medium - a lot comes down to the original production, soundstage, sound engineer, original mastering. Some of my CD's, non SACD, sound exceptional on my system...they were produced well, on a great sound stage, and a great first master, on par with my analog vinyl. A few of my SACDs - not so good. The same holds true in my digital music catalog. To try new things, I picked up a few CDs & downloads from 2L productions (Borders & Pax), as they are known for pushing the recording quality to the best possible = and yes they sound great both on CD and downloads:  https://shop.2l.no . PS Audio also has stated producing high quality albums...I have not heard  any https://www.psaudio.com/collections/octave-records

Streaming is the same - in my system; I feel if the original tract was done well to start with it usually sounds good.  I stream via Tidal, many of the 24 Bit/192 KHZ sound great, some not so. My digital library is the same...some good, others no. Even on U-tube music there are tracts that just sound exceptional in my system Steve Windwoods latest cut of "Cant find my way home" https://www.youtube.com/watch?v=eoSn2Y-b6wI, & also his https://www.youtube.com/watch?v=bXDcPoeIx-E&list=RDbXDcPoeIx-E&start_radio=1 or Christina Aguilera take of Moulin Rouge https://www.youtube.com/watch?v=RQa7SvVCdZk&list=RDRQa7SvVCdZk&start_radio=1

A few of my brand new "high quality" vinyl albums - just sound poor from the start. If you get the 170 pressing of an album, it is different than the 170,000 pressing. A few of my original albums from the 60s & 70s sound better than the newer remakes, actually – many do.

My analog system is still a little better than my digital system, but digital has made some great advances, and the margin is very thin.  At this point, recordings from top notch companies, such as Reference Recordings or Mapleshade will sound better than recordings from most other companies, no matter what format I choose to purchase  (or access if I'm streaming it).

@audio-b-dog 

No. It isn’t as involving as vinyl.