Is there any such thing as a bad sounding DAC these days?

I agree that most DACs $500+ sound good.

What matters now is synergy with DAC and the rest of the system. My Benchmark DAC3B which is bright on top is incredible on my warm RAAL VM-1a tube headphone amp. Not so great on more neutral gear I have owned.

I had the $24k Playback Designs Dream DAC in my sights but I had a nagging feeling it was not the best way to elevate the overall system since there are a lot of great DACs for a lot cheaper. I spent that money on my amp, a CODA #16, which was a very wise move. I got a Schitt Yggi+ OG DAC which has me totally happy with the DAC ($2800) and the PBD Dream is long forgotten.

What DAC’s from the early years of digital sound "hideous"? Inquiring minds want to know!

The Benchmark DAC1 is hideous compared to today’s DACs. I owned it for a long time, as well as the DAC2, DAC3 HGC. 

This brand many have not heard and is very good in all his price groups the MK2  i

am purchasing this week ,it is the most rewarding dac I have found under $10 k 

https://en.merason.com/

@audioman58 Great choice! I have considered the same one when I upgraded from the (Swiss) Merason Frérot. But then decided for the (French) Métronome Le Dac 2 which sounded a little better to my ears.

My subjective observation is yes, but...

Around 2000 DAC's universally improved how well they played Redbook.  The days of big jumps in sound quality between a 44.1/16 bit recording and 96/24 have all but vanished with only very small differences probably brought on by the digital filters.

Can you still make a terrible DAC?  Not sure, but while the Topping D90 (or whatever I have in a box) measures great I don't listen to it for long. 

Don't forget about how improvements in ADC;s have contributed to this.