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

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 🎶🎶👍

I think digital has made it to the point where it is very competitive. I also would not spend mega-bucks on digital as it is still improving and evolving. 

I have a VPI TNT-HRX with a Lyra Scala cartridge and Audio-Research PH-6 phono stage. I recently purchased a Roon Nucleus, Holo Audio Spring 2 DAC Kitsune tuned with the Kitsune Tuned Edition SU-1 DDR  USB digital to digital converter. 

If I have a MoFi UHQR and a hi-res download, the UHQR still wins. But standard vinyl pressings against hi-res downloads are often too close to call. 

This is roughly $5,000 digital front end versus almost $20,000 vinyl front-end. I still love vinyl, I still use vinyl. But to my mind vinyl is no longer cost effective. I am unlikely to buy more vinyl.

It was almost 18 years ago that Michael Fremer, you know, of Stereophile Magazine’s Analog Corner fame, declared that of the top five best sounding systems at the Big Show in Vegas that that year, four were digital. Hel-loo! Only one vinyl rig, the Walker/ Kharma room, made the top five. I’m not hot doggin ya! 🌭

Comparison's made with the same system cancel out everything except the variables being changed.

Except, how to escape the music being a variable itself when digital and analog are made from different (differently produced) masters? A fair comparison digital vs analog should include analog and digital sources made from the same master...

For digital it is relatively simple. It is all about the DAC. Any good transport will suffice. 

Possibly in a world of CD transports it's closer to reality; however there's comp audio, which is more interesting because of its openness to all the existing digital formats and resolutions...