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. 

I have had 2 of the top Topping DACs a few years ago. It was not a great DAC but not terrible either. It was much better than the DACs that are in most integrated amps and cost a lot more. A warm system helps keep the Topping in check.