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

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)...

tzh21y As for your question...I spent under 5K for a Lumin T2 w/ external power supply. I can't tell the difference vs. analog. Lumin T2 has a built in dac. Amp is tubes.  

As for "I have heard some very high end digital front ends" ...were those piped into tubes or SS? And what about all the rest?

As for the analog vs. digital conundrum. I would love to read, go to or see a blind listening test of a analog/digital rumble by an august bunch of audiophiles (Old gals/guys)...That would be something!

I suspect vinyl love has an innate component of the undulating subtle variance of the sound. In other words the slight ever so subtle imperfections (minus dirt, ticks and pops) of vinyl has a darn attractive quality. Digital sound is "even."

Picking a CD Player / DAC

1) Pick 3 music selections that (a) push your buttons, (b) make you come alive. (c) are like a fountain of youth for you. These selections will be different for each one of us and they should not be longer than 15 minutes in total.     
                                                                        
2) Take your personal CD player or DAC to 3 different Dealer Salons or friends places.                                                                     

3) Insert your CD Player / DAC into the chain first (very important) and listen to the music. This allows you to "Form An Opinion" in their "Room" with your gear and music as input.                                

4) Now - try the music with their CD players, DAC's, ...                     
If they allow you to bring the gear home - highly unlikely - even better.

If their gear, does something better for you - then you know what gear and the cost.    

3 music pieces and 15 minutes of music is important.  I found more than 3 was too much to take in. Also 15 minutes allow you to be out of their hair within the hour (if at a Dealer Salon)