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
My Sonic Frontiers Mk2 was/is making scratching noises...so I started using the Dacs in my lecicon mc 1
The SF uses a 1996 vintage 20 bit 8x oversampling UltraAnalog D20400A (1 Dual) ... while the Lexicon MC 1 uses a 2000 vintage 24 bit 96K Delta Sigma DAC

I am on a very tight budget these days and was just assuming that any modern dac would be superior to my vintage pieces. Not worth putting more money into them. It sounds like, I should re tube the dac because it would take about 3K to equal or do better. Is that about right??

What would be a good USB to spdf converter to use these days with either DAC??
@tcatman

There are a number of $2K dacs you should consider. Especially if you have a lot of Redbook to play.

Mytek/Schiit/Ayre

iFi makes well respected USB--> SPDIF converters.
I think the biggest common misperception is that the type/model of the chip set in a DAC (or a CDP) makes the most difference in its SQ. Aside from the choice of components, e.g., capacitors, resistors, etc., the main reason these "older" DAC/CDPs still hold their own is because of their uber quality power supplies, analog sections, and mechanical isolation/damping in the transports sections. Chip set (designs) come and go.... and keep getting better. The current multithousand dollar DAC/CDPs are the ones that have the best of the stuff used in the older gear plus the best of the current (chip) designs. More power to the folks who can afford them.
Exactly kalali. The fallacy that the D/A chip is the major determinant of sound quality leads folks to the wrong conclusions/decisions regarding the sound quality that different DACs provide.

I just bought a (used) Hegel HD-12 ($1400 MSRP) and have spent 2 days thus far listening to it. I find it to sound very good streaming Masters from Tidal. Before I bought it, I researched the D/A chip (AK4399) utilized in the HD-12. It was AKM’s top D/A chip two years ago and was also used in the Esoteric D-02 ($23,500 MSRP).

The AK4399 D/A chip itself can be bought for $22.50 and complete DACs with this chip are being sold on eBay for <$200. Does anyone expect these models to sound like the Esoteric D-02 or even the HD-12. I hope not.

So, what’s the difference in the <$200 DAC and the $23,500 Esoteric D-02 that both utilize the same AK4399 D/A chip? The number of chips utilized, the processing algorithm, the filters chosen, the segregation of digital and analog circuitry, the buffer amplifiers, the power supply/power regulation/noise rejection circuitry, the quality of components other than the D/A chip (especially in the analog section), the flexibility of input options, the enclosure, etc.

Dave