One DAC to Rule it All

I’m with @soix ​​​​@ozzy62 .  Why so involved?  Now, to play Devils Advocate, I doubt that anyone here has actually heard a setup like yours, and your ears are the ultimate judge, but the conversion back and forth would be enough to drive me nuts 

Convoluted? It's really nothing more than an active crossover (in digital form) splitting the signal between my mains and subs at 100Hz. I realize I could send the full range signal to my main speakers, and just use the DBX to the subs, but as I said I had done that for a long time and recently found that keeping the <100Hz from the main speakers gave me a nice increase in resolution. Other than going to a DEQX Premate to do all these features including the DAC from my server, I don't see any other way to get a 48db/oct. slope out to both the mains and subs for a reasonable cost. Also a 48 db/oct crossover in the analog world would be quite a complex and convoluted thing as well.

I also want to thank everyone for sending in their thoughts. I suppose dipping my toe into the digital realm more than once is considered blasphemy in home audio, but I am getting very enjoyable sound. I am considering the DEQX route as their internal AD/DA are of a higher quality. So even though I am seeking advice, you're all correct in the fact that I just have to try out all these configurations to see for myself. I will experiment and keep everyone apprised.

From my medium technical understanding, the main concern with digital replay is jitter, which is largely a function of timing, followed distantly by sample rates.

A large culprit in jitter is a mismatch or misfit in the clock or something effecting timing, from hardware limitations to design issues to noise from various power sources.

Every truly resolving system I’ve heard had separate, but matched, streamer and ;DAC in a different box with an external or otherwise isolated clock.

Nagra, Lumin, Esoteric would be what I’d be looking at, probably Esoteric for all components.

The only thing I know is that, under certain circumstances, multiple ADC and DAC conversions do not substantially degrade the sound.  I heard a track on a test CD (a Jazz sampler/test signal CD by Chesky Records) that was of a sample of music that had been converted back and forth a hundred times, and the same track that had been converted only once.  I don't think I could reliably tell the difference.  

I don't expect the additional conversion of the OKTO to hurt the sound much, but, then again I don't see how it would help to take a digital signal and convert it to analogue then have an ADC convert it back to digital for processing in the DBX.