How to get into high end digital? (Feeding a DAC)

OP glad to see you are setting in on something amongst all these what I will call various responses.  Sign up for Roon after you rip and get the AVR setup.  If you are going to be using the coax or optical out will really limit your range on an external DAC. No high res I believe. Need usb.  
My suggestion would Play with before you do anything and see if you like Roon. If you do new DAC unless your Avr is serious hi end then a new DAC would be great. Feed it back to avr to amp via analog pass through if it has it.  This works great and you can find the right DAC.  For your budget it’s wide open.  
Good luck. 

I have read all of this but have a question. I have all my cds stored FLAC on my Synology NAS. I stream music through SONOS through the house being happy with the general outcome. But for my serious listening I feed to a SONOS Connect to my main stereo. The feed goes to my Bryston dac, then to my Cronus Magnum. Am I missing anything here? How can I make this set up better?

So the Snology would be like my NUC?The Sonos like rather Roon?
And the DACS gets the optical from the Sonos, where I amight do it from the AVR?

@lbarbish
Your question is off the OP topic which is generally frowned upon - you’d be much better served by opening a new thread with your inquiry

If it is a serious question, then it seems like is similar.
Or is it sarcastic?

Or do the Sonos output into the DAC, do some known jitterbug dance?

@lbarbish my post at the bottom of page one of this thread (last paragraph & the 2 youtube links) answers your question. If you watch and have followups, happy to help in your new thread. Cheers,
Spencer

The deeper you dig,the bigger the whole.Go simple ....