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

I listen to about as much digital as I do analogue, although I go through periods where I listen primarily to one or the other.  I'm VERY happy with the PS Audio Directstream and the most recent iteration of its FPGA programmed DAC.  It sounds less digital than anything else I've ever heard and is now on a par with the DCS products for far less money.

I find the complete opposite.  Digital systems say under $1500 sound much better than analog - at least vinyl.  But once you get over about $3K vinyl starts sounding better than equally priced digital.  

as asked the question is not answerable.

there are so many levels of analog that you can't really say. i have what many consider to be the very tip top, bleeding edge of digital performance. yet, my best vinyl or tape easily surpasses it.

however; at more modest levels of analog there are cases to be made that digital can somewhat go head to head.

if you want to really understand where digital comes up short consider the limitations of digital recording, read this Stereophile interview from 1995 with the principles of Pacific Microsonics. especially read toward the bottom of the first page. you might think you know as much about music recording as these guys, but......you don't.

http://www.stereophile.com/content/hdcd-keith-johnson-pflash-pflaumer-michael-ritter

Gas car?  Electric car?

Unless the listeners ears are between 17 and 25 in biological age every nuance of difference even in CNO systems is impossible to convey.  The actual population discussing this will talk about jitter or filter harshness or wow and flutter or dynamic range etc. and theres too many structural issues to resolve attempting to normalize two very different forms of source media.  Whatever yiur setup is, if you like how one sounds you will become accustomed to the other but circle back to your original preferences.  Im not familiar with anyone devoting close to equal time with analog and digital.  For me, analog is the special occasion champagne while digital is the daily driver...the mixed analogy is intentional.