is it possible to make digital audio sound like vintage vinyl

The problem here is why do you want anything to sound like Vintage vinyl? Don’t get me wrong, I’m deeply committed to vinyl, but I want my vinyl to sound as close to state of the art as my budget permits. And I think I’ve come very close. My digital front end is, I think, state of the art. And I can honestly say it doesn’t merely sound great “for digital”- it just sounds great! 

To make digital sound like vinyl, just digitize an LP.

Short of that, you have to make your limited resolution 24 bit files into infinite (0 samples) resolution files. I don’t think that’s possible.

Let’s assume your vinyl rig is at least B+ quality or higher (TT, arm, cartridge all pretty good)--and it’s optimally set up--and if it’s a moving coil or low-output moving iron cart, the step-up device is also at least B+ quality. That’s a lot of assumptions, complexity being one of the unavoidable facts of life of good vinyl.

Can you make digital sound more like that? A very qualified YES. Qualified because no digital device will ever match the slightly phasey vinyl sound, complete with surface noise (from imperfect channel separation, boulder being dragged through grooves, etc). But you actually can push digital to be somewhat warmer, more spacious, and more satisfying tonally & timbrally. Easiest way is to get a well designed/constructed NOS (non-oversampling) DAC. A well designed/constructed multibit DAC will probably suffice, too.

My NOS DAC is MHDT Labs Orchid, which includes a tube buffer circuit (I swapped the stock tube for a recommended new-old-stock tube). I no longer hear any of the digital nasties I thought were baked into digital back in the days I had delta-sigma DACs.

In all fairness, there are any number of overbuilt, uber expensive delta-sigma DACs that people rave about as being highly musical and un-digital in sound. I just can’t see spending >$15K to get to more or less the same more-like-analog place my $1,100 NOS DAC does.

Did I mention how good digital cassettes sound? The best of both worlds. Great SNR and dynamic range and more analog than digital. Almost as analog as Pure analog Cassettes but no air I’m afraid. 🤗

sam here and let me say that i hate the side effects of vintage vinyl (1970's) however the sound is alive . i have not tried an expensive dac and that might be an answer?

the fact that vinyl can't be brick wall compressed for the loudness wars has a lot to do with vinyl sounding alive? 

 i downloaded a digital rip of a vintage vinyl record with a song on that record that represents the exact sound i'm looking for. not the song itself but the tone and the sound stage here is the hi-res vinyl rip.
http://u.pc.cd/xUYrtalK  now here is the commercial digital download of the same song. http://u.pc.cd/QzrctalK   the vinyl version has a dynamic range (12) digital version (5) that has to effect the sound quality? the digital version is unlistenable to my ears.