How much do you need to spend to get digital to rival analog?

35 yrs ago I had a fully vinyl rig set up to compete with a heavily modded magnavox player du jour (which did sound way better than other players of the day). I had many vinyl/CD repeats and auditioned them extensively, one after the other (through a big tube amp & Vandersteen 4 speakers). Digital always sounded different from vinyl in way described above, and to my ears, vinyl usually sounded better. But it was easy to see the vinyl recession that would follow--vinyl would no longer be ascendant. 

I formed an opinion then that still holds up, though my audio gear is vastly different today: that is, if I had a vinyl system, I would put serious $$ into the TT & cartridge, also the phono preamp--because the extra outlay could be heard relatively easily. But with digital, I would keep it mid-level, never plunging on the big-$$ brands of the moment. Beyond making sure the cables were good quality, I'd upgrade players from time to time, rather than going for any one SOTA player.

And so it is today in my desktop audio system. No vinyl here (no room). I use DACs pretty much as I did CD players back in the day. I'm fond of non-oversampling (NOS) multibit DACs & am on my 2nd. Its sound is very fine for digital (MHDT Labs Orchid @$700). I have no urge to upgrade. My passive studio monitors are very high resolution & sound wonderful to me in the current setup. I listen to a lot of streaming music, also 100s of GBs of music I ripped to the HD.

One thing I would certainly try if I had a vinyl front-end (1500 LPs in storage) is to rip vinyl recordings to disk, then output through DAC + speakers. That would be very interesting, to see if the positive attributes of vinyl survive digitization.

There are audiophiles who swear by analog. The other day, I saw, in a coverage of the AXPONA show (If I am not mistaken) a TT that costs $130,000! There was a debate in the forum about LP's that were mastered digitally. I find them to be as good as those that were mastered from Reel-to-Reel decks. I am one of those audiophiles who are annoyed by the clicks and pops when listening to Vinyl. The only way to solve this is to buy an uber-expensive FM Acoustics Phono Stage - they supress the clicks and the pops. As for me, my TEAC CDP3450SE CD Player (with ken Isiwata teaks) sounds as good as analog. No grain, not analytical, just a warm, articulate sound. But I want to share with you a simple, cheap setup that I have devised. I bought a 1USB to 3USB splitter ($20), and connected it to a USB port at the back of my PC. from there, I connected a cheapo ($5) USB cable to my humble integrated amp. All I have to do is type the name of a concert, album, song, in any genre, in Cortana. The source of the  files is YouTube. Now, You wouldn't think that a $25 setup like this is a recipe for a good SQ? Surprise Surprise, the SQ is excellent! My mother, my brother, and myself were impressed by the SQ. No need for a costly streamer, this set-up does the job beautifully!

I have 25,000 LPs, 7,000 78s and 7,000 CDs.  Sure, I love playing analog.  As of yesterday, I now have more than an analog-like sounding CD front end (EAR Acute).  I purchased a COS Engineering DAC (D2).  I have entered to realm of great digital playback.  As mentioned, digital can be sonically uncolored unlike most analog gear.  My new DAC is not 100% perfect but it allows me to hear music with a unfettered/untethered frequency response, dynamic contrast, soundstage, tonality, resolution and imaging.  I wonder if it's pacing could be bettered.  There is so much music I was missing, the subtle sounds that my best LPs have.   Moreover, this is the first time that I can enjoy music from very soft to very loud sound pressure levels (my system should have been able to play quietly did not until now).  My friend Grover Huffman has the H1 and last week showed me how fabulous my system could sound.  I got pant flapping bass without distortion, wild dynamic contrasts and an ability to listen for 4 or 5 hours without listener fatigue (his demonstration led to a very long listening session).  I should mention that I have Grover to thank for his all silver RCA 75 ohm SPIF cable, his Pharoah A/C and RCA ICs which I own.  I enjoyed the EAR from 2006 with it's rich, lively sound but it has been eclipsed by the DAC.  Warning-this DAC is not forward sounding to bright.  The plane of the sound is between the speakers.  Digital playback cannot make a mediocre or poorly mastered CD sound great, but I have so many great CDs that it is as difficulty to choose music to hear as it is in the analog realm.  

I agree with geofkait re cassettes. Holly Cole's "Temptation" sounds as good as any CD or LP in my collection when played on my Tandberg 440 A. 

I totally disagree ,if you listened to the Zlatest Lampizator Vacuum tube dacs 
with top quality USB cable which is essential to bring the realism out
I highly recommend the Final touch Audio- Callisto usb, and their great interconnects.  Records lack in many areas for example a record at best 12 bits
digital almost double Thst, dynamic range No contest, Bass also .
and in a proper setup the warmth of the tubes and  greater resolution ,
as well as not all the added headaches of cleaning records, storing a wall of vinyl.
i just get my tablet and play. A good turntable setup is well over $5 k 
the entry Lampizator with upgraded tubes ,power cord and usb is about $5k.
at $5k with full turntable setup and cartridge ,That is maybe average for a decent turntable setup , which I heard many , and I would never go back to a turntable
too much added labor and No sonic benefit IMO. Some reviewers are jaded for their hearing likes a duller warmer foundation , your cartridge can tune your turntable like a different Vacuum tube can flavor your system .
one person likes a more defined leading edge, where another prefers a silky smooth midrange ,that too is why we hav3 Vacuum tube Amps preamp ,
land solid Stste many times mixed Solid-state Amp,Vacuum tube preamp
you system cables ,power cords all have influence . That is  why you hear many 
good systems ,and vinyl had maybe 10% of music selection of high res DSD
or cd . And far more expensive ,and need a room just for storage. If you like Analog good ,I prefer good digital .go to a show where Lampizator or other Highend digital is playing for sure you will hear a major difference ,
I do agree that vinyl will sound better at the lower priced setups , but once you start approaching over $5-10 grand the gaps closes fast ,check out the $25k 
Lamoizator Pacific,or Golden gate World class  sounding music Period 🎶🎶👍