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

Depending on Budget. The Excellent Lampizator vacuum tube dac 
which received a 5 star rating in Enjoy the music .com 
is their latest entry level dac that is $2750: and by far the most natural sounding dac under $5k. If your budget can go higher their next step is around $6-7 k. The key is very good USB cable 
they distribute a small little known brand a Final a Touch Audio
Callisto usb cables by far the best cable I have heard and nothing under $1500 can beat it for its natural presentation especially after 
150 hr runin , it was so good I bought the cable ,their interconnects are just as good . Check out the Lampizator Amber3
dac .they even have a money back guarantee, and the USB  cable 
at around $800 a must if you want to hear proper digital thst sounds like good analog.

About $25.

Lemme bring my AudioEngine B-1 to the shootout and I’ll win this horse race for pennies

IMO - The dilemma for the Audiophile, is that this is not a horse race, but a marathon.

The Op has already said he has heard great digital - in short spurts.
I will say it again I blame the engineers. They were given this gift when CD came on. They just didn’t know how or were not allowed to "play with it" , especially when it comes to the popular music genres. Now, if I did not have my vinyl rig I probably would not be saying this as my digital sounds just fine - when all I do is listen to digital. But then I will introduce that archaic black plastic disc....

And, when one does come across music that has been recorded well on digital. You know it when you hear it. It has a presence. You cannot stop listening to it. Concentrating on it. With this kind of digital recording all it takes is a good CD player to bring it out - imo. I believe everyone has examples of this type of music. The problem for me, is that this music is usually an obscure recording, and not the music I grew up with. So I can only listen to it so many times. When I hear music I grew up with, it brings back good memories.

You have not heard a proper setup then , You didnot state how much $$ spent on complete turntable setup ,that is key
for under $4k the new Vacuum tube Lampizator vacuum tube 
Amber 3 dac, and a Must their Callisto USB cable try that ,
look at the reviews. 

Apparently you just have to know what you’re doing. 🤗