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

This or a similar question appears on the forum with regular frequency.  It makes for good reading every time.   I hear what you are saying.  I agree that the majority of digital rigs, even ones that are quite expensive, struggle to produce the magic that seems to be unique to vinyl.   It is possible to get engaging, non fatiguing sound from digital.  It is more a case of careful equipment selection and system matching than how much you spend.  I have a Modwright Sony HAPZ 1ES that makes beautiful music that I can listen to for hours.  Tube selection  is critical.    It takes work.   At the end of the day digital won't sound like vinyl, but it can be very satisfying with the right equipment.

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?