Are "vintage" DAC's worthwhile, or is this a tech that does not age well

I own 6 DACS of varying shapes sizes and usages, ranging in price from $100 to $500, and I sheepishly admit that I can't hear any differences between them.

That said; I can hear the difference between a budget DAC/amp and a pure DAC paired with a decent amp.

 My most recent purchase was the Gustard X16 because I wanted a decent DAC with Bluetooth for my YouTube friends. 

dacs definitely have distinct sounds... obviously one needs a good, resolving, proper set up system, decent recordings and some listening experience (and good hearing, of course)

dacs are not just about converting 1’s and 0’s to analog waveforms (even this process has several discrete steps)... they also generally contain an internal line level analog amplifier (and thus, also, a power supply to that amplifier)... these output buffers and/or amplifiers, just like all amplifiers, have output impedance which must work with the input impedance of the receiving device -- this is why they sound different, just like different active preamplifiers/linestages sound different

the sonic differences are certainly more subtle than differences between loudspeakers, or phono cartridges, but are more distinct than among, say, different solid state amplifiers or phono preamps

I currently own the Denafrips Ares II DAC and it sounds very good. More 3-dimentional, wide and deep soundstage with good separation of the players. And it has a phase reversal switch for those discs that were recorded in reverse phase. I listen to classical and operatic music where its strong points can be appreciated. I've had many DAC's in the past and I feel their entry level is very good. Don't forget the SPDIF cord; it's  quality is very important. 

The current generation of DACs are all measurably better than their predecessors, but you may not feel that is important.
There is better understanding of clock architectures including phase behaviours. There is also better understanding of how noise is handled.
For Red Book discs and files (44100Hz), how the "brick-wall" filters are implemented should have audible impacts.

DAC chips age well, in fact many of the best DACs made today employ old chips. My personal favorite is the CAD 1543 MK ii which uses 16 of the old Philips 1543 chips. 
Advances in understanding of power supply isolation, usb integration, and EMI/RFI, mean that new DACs using the old chips is often the sweet spot.