High end vintage vs contemporary DAC's - are sonic improvements real?


The vintage DAC question seems to arise regularly, more or less along these lines:
     "I can get an old XYZ for $2000 or a new ABC for the same $$.  What to do?" 
The answer almost always seems to be "go with the new ABC, the XYZ is older technology," "digital has improved enormously," etc etc. 

Obviously digital technology HAS improved enormously in the last 20 years (or even 10 years, or the last week depending on your belief system).  Sampling rates have marched upwards (though many will say that anything over 24b/96khz is a waste, and I agree) and everything has gotten cheaper and smaller.  Music servers have evolved and storage is cheap.  We have streaming now and use phones as remote controls to manage infinitely large music collections.  The list goes on and on.  Yet in my mind it's really THIS stuff that's embedded in the assertion that "digital is much much better than it used to be."

But how many people have actually compared a high end DAC from, say, 1996 (now selling for $1500), with a new DAC for the same $$?  Sure, features won't be the same - the old unit won't have USB anything, higher sampling rates, etc.  Yet for all that, I can't recall any conversations on actual apples vs apples comparisons of new vs old, especially on the **same** source material, specifically on a Red Book CD or a lossless CD file rip.

Example: In 1992 the Mark Levinson No.30 DAC was sonically at the top of top for Red Book CD reproduction (feel free to substitute your favorite DAC of that era).  Fast forward to the present. How much better does today's DAC de jour sound playing that same CD?  Sure, source file X recorded and mastered at 24b/192khz will likely sound better than the same file downsampled to 16b/44.1khz when played on a decent system.   But will a Red Book CD played on a new DAC sound better than the same CD through that ML No.30? 

To be clear, this isn't about sampling rate or format wars.  Think of it like this:
Let's say I have 15,000 CD's, that's all I ever want to play, and I've $3000 to spend.   What would I get for the same $$ that would sonically do as well as the No.30 playing the same CD?  Is the answer "almost anything, because sonics have improved so much"?  Or maybe it's the $10k such-and-such.  Hopefully this illustrates the question.

Comments and thoughts would be greatly appreciated.
raueda1
Ive heard the modded trivista from parts connection it hits wayyy above the cple g investment
and it 10 yrs old
All you guys are convincing me that trying to improve on the SFD-2 MKIII - which is "free" cause I already have it - would be very expensive at best and maybe not result in meaningful improvements anyway.  That's a happy outcome cause it makes my life easier, thank you very much!  Thanks for saving me a lot of money and effort!

[sidebar - interestingly the SFD-2 MKIII uses the same OPA627 op amps as the modded Trivista.  Those boys at Parts Connexion do know their stuff.]
@raueda1 I can't find much online about the Mk3 but the Mk2 version of your dac looks pretty killer very robustly built with a serious looking power supply! And some great reviews as well. Assuming the Mk3 is built along the same lines it's undoubtedly a very fine dac that might indeed give modern dacs a run for their money. Here's a thought rather than improve on it perhaps improve it? Parts Connexion does mods on SF gear, why not see if there is a mod they recommend for your dac?
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raueda1 -

The short answer to your question is easy: No.  You will not get better sound from Redbook CDs than what you have now without spending more than $3K. 

I use a Meridian 598 DP as transport into the 563, and the combination sounds very good, and on Redbook CD is competitive with most of what's available today. 

So stick with your SFD.