Worth pursuing analog sound from digital?

I’m a confirmed vinyl guy. Two turntables, three tonearms, more cartridges than I can remember. I’m also in my 60s and been collecting records since the early ’70s. But I’m here to tell you, vinyl takes a lot of commitment, with a pretty steep learning curve, before it sounds truly great. Don;t get me wrong: I love every aspect of spinning LPs. But still.

I also have two systems that are digital only, with one dedicated to streaming Tidal. If I were starting over today, I might just go with Tidal. Sounds pretty fantastic, and you can put together a dynamite system for very little outlay, relatively speaking. Neat, clean, small footprint with no media taking up space. Constant churn of new music to explore. It’s a game changer.

big_greg hit the nail on the head. 

I love both and listen to both. 

In the end when was the last time, in quantity, recordings were made all analogue? maybe 25 years ago? so when was the music you listen to made? 

I have a new production Mark Knopfler album (Tracker) on both Vinyl and streaming "master files" via Tidal and both sound excellent but to my ears and system the master files on Tidal take it for sound quality. Not by a huge amount but enough in detail and frequency extremes to be noticeable. (Schiit Grungnir Multi Bit DAC). oh fyi Joni Mitchel has some excellent Master files now on Tidal as well that are worth a listen, and better then the records IMO. 

Now streamed hifi quality on Tidal (CD quality stream) of let say Santana's Abraxas and its no contest the vinyl is much better, fuller more liquid sounding . 

So is it the Digital - analogue  or is it the recording era that's the make or break for Digital sounding as good or better then vinyl?  

I'm thinking modern digital recordings have it over older recordings either digital or analogue. 

I really think its about the quality of recording apposed to the format. Both can and do sound great and not so great. 

@jaferd.
I owned the Nuwave DSD DAC and was never able to remove the harshness or "edge" from my digital sources. I played mostly CD and some files from my Mac.
It would help if you told us what your digital source is.

I tried different CD players and finally upgraded to a transport. I still wasn’t satisfied with the sound; it always had a digital edge. In my case, it could have been that my components lacked synergy, but I knew the dac was part of the problem.

I’ve learned how important the digital cable between source and dac is. I could hear the difference in SQ with the various cables I auditioned.

I started to read about all the R2R multibit DACS that were coming to market. I picked one up and I finally had a non-digital sounding system.
And after some upgrades I believe I have a digital rig that rivals analogue.

I must mention that clean power plays a vital role for digital to sound its best.

Here’s the thing I cant figure out. Listening to the same track (same mastering, spl, etc) on my digital or analog is extremely close to my ear. Yet I don’t ever listen as long to the digital stream. Maybe an hour max versus hours on vinyl. So is there something that my ears can’t detect that my brain can? Or does the digital interface itself tire me in a way that getting up from my chair doesn’t?

Pick up a MHDT Orchid R2R Dac for $1100 from LTA. It sounds great and is better than my previous PS Audio Direct Stream Dac which lists for $5k. It comes with 4 different digital inputs plus it has a tube stage. Buy a NOS WE2C51 or WE296A tube for less than $100 and you’ll have a great sounding system.

I convinced Grannyring to buy one and he absolutely loves it.