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

Everyone has to remember that now it is the rare recording that is done analog. The vast majority are now recorded directly to a hard drive. So in saying that analog is better you are also saying that high resolution digital is not a problem and that analog playback of digital material is better than digital playback of digital material. I believe this is an admission that vinyl playback is adding something to the signal that many audiophiles prefer be it the background noise that dithers our brain or increased distortion (added even order harmonics). There is a euphoric quality to vinyl playback. Another interesting comparison is older analog recordings vs newer digital ones, a very difficult comparison to make because you can not get a single piece recorded both ways for comparison. In thinking about it I really could not say. Most of my classical collection is analog and given that I was very picky looking for the best artistry along with recording quality, it is an excellent collection. But, what little DDD I have is also quite good. I have the four Brahms Symphonies in 24/96 digital and they are wonderful. I can not imagine it getting any better. But I also feel the same about many of my analog recordings.

     I know this is not exactly what you mean, but to answer your specific question, buy a CD player that costs as much as your cartridge, tone arm, record platter, phono pre-amp, head amp, assorted isolation equipment and wiring.  
     For your question, total all these up and compare the total to the price of your streamer, which BTW, I am not convinced would work, being on my list of inferior products, along with horn speakers. 
     Don't anyone continue to ask me to consider horns by saying I must hear yours, without an actual invitation; ditto for your streamer.  I have heard Audio Advisor's (WPB, FL) streamers and am not impressed, even though they carry the best equipment I ever heard (Wilson, Audio Research, B&W 800 series, and much more, along with the $27000 turntable at their entrance, and $1500+++ LP's to play on it. 
     Am I a total snob?  Not really.  I even listen to the inferior XM radio through my 803's, because I Iike the jazz station, and drive an old, blown S2000S.     

Are you saying that a CD transport or CD player is better than a streamer/DAC?

Let's have some real world stories, at the price point suggested by tzh21y.

I have a vinyl front end at the 3k price point, with an excellent phono stage. My CD playback did not rival it until I purchased a stand-alone DAC (Border Patrol). That investment was enough to create parity in listening pleasure. No huge bucks necessary, just a symbiotic purchase. The same music that I own on both CD and LP, sounds sufficiently pleasurable, not identical. This is the first time I've managed to do it within my mid-budget system.

I have recently gotten a dcs Bartók DAC, which I’m using in conjunction with a Roon Nucleus. The cost was about $15K, and for the first time the sound rivals, IMO, my Clearaudio turntable/tonearm/cartridge with a Nagra phono stage which was about $10K. To my ear the vinyl still generally sounds better, but the difference is pretty small.  That is playing ripped CDs and some downloaded hi-res files though - if I stream music (using Qobuz) there is a definite (but generally acceptable) step down in quality.  My experience anyway (and ears)...