Digital Gear & Upgrade Question, What do I need?

You have tremendous opportunities for improvement. I spent about fifteen years moving from PCs and NAS etc to a good sounding system. I was reluctant to upgrade the streamer portions. Wow, I really wasted time.

You have really good equipment. I recommend stop fiddling around with PCs and JRiver stuff. Borrow, demo, or buy a good Aurender Streamer (or Auralic). You want to put a streamer in the loop that is on the same level as the rest of your equipment. You can put money into internal storage on the streamer… but seriously it is a waste of money in getting anything but the minimum. Streaming off the internet will sound as good or better than locally stored red book CD files. For $14.99 / month you can have access to virtually all music (including what you own) in as high or higher quality.

I used PCs, MacBooks.. for years thinking there should not be a difference… I was so wrong. Given the great quality of your components, I recommend looking at a Aurender N10. It should fit in well with the rest of your system and upgrade the sound quality of your whole system to it’s capability.

I appreciate the information, took a fast look at the N10 and as an owner of said equipment I have a couple of questions. I am guessing that I would retain the PSA DSD for the DAC or is that all accomplished onboard? How does one go thru their current library, the thought of scrolling a small screen is not very appealing. Can it be accessed via a tablet for function like search and play?

Obviously I will need to do some additional reading

You could benefit from upgrading your server and upgrading your DAC.  You will find the DSD is a wonderful unit but older.  Newer units can give you more resolution and bigger, more engaging sound.  I would encourage you to look at Bricasti.  Both the M3 and M1 SE are big steps up from the DSD and Bricasti’s sound profile would strongly appeal to you.  There are lots of other DAC options that would be a step forward, but my experience is Bricasti is an ideal next step for DSD owners.  
 

a server will deliver a cleaner, clearer sound to your DAC.  Something like the Playback Designs Syrah would be a very good choice given your preference for JRiver.  You can consider other servers and software.  Roon Core as the server using Squeeze as the interface is generally deemed a very good, if not best sounding option.  For that, something like an Antipodes S40 or K30 would be excellent.  I know those are radically different price points but you haven’t payed out a budget.  S40 is good.  K30 is great.  K50 is elite.  You get the idea.  
 

In general. High end systems like yours normally will have a separate DAC and streamer. Music management goes on from an iPad. Aurender is known for having a fantastic app. Great for exploring and creating a library. It will cateloge all tunes on local storage, on your network (NAS) and you can add all the streaming albums and tunes to it.

To get the most out of streaming you need a very high quality DAC and streamer. I highly recommend a used Audio Research DAC… perfect complement to your system. Incredibly musical and detailed. Given your budget… if I had to, I would look for a used ARC DAC and either a used Aurender N10 or drop down a level in Aurender. But long term a contemporary N10 or better. They redesigned the power supply on the N10 a couple years ago. Probably making some of the older ones a bit more affordable.

I just want to mention, I have been a long time Audio Research fan for preamps and phono stages, and Pass for amps (last x350). then over the last few years one by one I swapped my components for Audio Research… the wave of surprise and happiness that came over me at each additional ARC component was incredible. Each time the synergy clicked in. Now, with all ARC components my system is the best I have heard. My dealer’s as well… although he sells a lot of stuff that costs more and installs many custom systems of greater value.