Quest for an external Dac has resulted in me way down the rabbit hole

Some good choices for consideration but the issue is that you may get one of these good ones and then decide it's not altogether impressive with your current system.

IMHO, that's the risk you take with your existing setup. I would suggest a RME ADI-DAC 2 which is available reconditioned or nearly new at your price point.

It is so flexible and brings so much more to the table than the others. You may land up making changes in other components but you will keep the RME.

Currently, I run it in a full-range system with rebuilt monoblock tube amps. It's a great match and no need for a preamp; the RME is a great product and great value.

Best of luck in your selection and happy listening. 

+1 for Denafrips, Alvin at Vinshine Audio is a pleasure to deal with, excellent customer service. As with any system, it's a balancing act to find components that complement each other so Benchmark may be good in one system whereas a Denafrips may be better in another.

I have a Denafrips Terminator Plus and it is amazing.  Before that I had a Wyred 4 Sound DAC2 DSD SE and an upgraded Schitt Yggdrasil.  The W4S was much better with more meat that the Yggrrasil.  You can pick one up for less than 1000.

see you you can get a listen of the Chord Qutest...

Truthfully, you will only know when you listen for yourself in your own home with your own system.

Once you realize the importance of the external DAC you will likely be switching them out like speakers for the first year of two. And they are much easier to switch out than speakers.

Start cheap, Like in the less than $200 range to see what everyone is talking about.

Having said that. The real center of the universe of quality without diminishing returns of money vs quality of sound hovers around the $1000 mark. I have owned and can highly recommend the RME ADI2, the Denfrips AriesII. My own favorite in that money range group is the Schiit Gungnir, frigging love that DAC.  All three are different from each other and wonderful with no negatives.

Now I am running the Schiit Yggdrasil OG. Purchased for $2100 used. For me my endgame DAC.

Final note. They all do sound different. And super great measurements don’t count for much in the equation. I purchased a super perfect measuring DAC reviewed by Amir (who I trust), that measured great, sounded like mud.

You have to hear these yourself.