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

ring dac or ’multi-bit/r2r/ladder’ dacs. (the one dac type goes by 3 different names, overall)

that’s the starting point.

then, excellent clocks, and excellent analog and digital circuitry to support those dac types.

Then digital can be good enough to enjoy as much as analog, without having to ’work at it’ (re enjoying). But it takes some doing. Not necessarily expensive, just properly made.

I’ve got a $2-3k modern 20+ bit multi bit dac here (stock, untouched), that I have not bothered to turn on, as it cannot compete with my highly modified 25 year old 44/16 bit multibit dac.

The question is moot because it assumes analog is inherently better which it isn’t. It all depends on both sides.
Having said that competitive digital is more common these days than not so even a minimal investment can take you far.

It all comes back to the recording, and the disc. Ya know, there ARE plenty of bad sounding LP’s. Besides, if an album is available on CD only, what are ya gonna do, deprive yourself of the music just because you think analog sounds better than digital? Are we sound lovers first, or music lovers?

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

Define "rival".