Digital Gear & Upgrade Question, What do I need?

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.

A nice relatively easy upgrade would be  Roon Nucleus with Roon subscription into your present dac, pretty much plug and play.  Sound quality improvement with this easy peasy setup would be substantial. Get a linear power supply for Nucleus, another nice step up.  A cheapo tablet like DragonTouch through Amazon would be used as interface. Your dac could also use upgrade, I won't even attempt to steer you here. 

Small green computer

@stevea11757 -You have awesome downstream components. I had a 5SE and have heard it paired with your Pass. They are a great combination.

Considering the musical quality you get from these, I would choose Aurender and a DAC like  a Musutec 005. These can be had within your budget. There is synergy with your existing components.

I have an Aurender and just purchased the DAC mentioned and am just so pleased by the overall sound quality. Check out the threads in the digital comments for more info, if this piques your interest.

All best,

David

IMO, what you really want to get away from is streaming using Bluetooth, as that's most likely using lossy compression.

Personally, I use a Raspberry Pi with Volumio for streaming duties. I can cast from my phone (YouTube Music, Qobuz) via BubbleUPnP to the RPi. I also added a shared folder as a source which I can access through the browser-based interface. The bits get converted by a USB DAC.

If you'd like to experiment a little before buying a dedicated server and you're somewhat technically inclined, try installing Kodi (free open source) on a spare machine if you have one. It has similar functionality to Volumio but can run as a Windows app. Connect a USB DAC to the PC and hook the DAC up to your stereo. I use Kodi on a system based around a Mac mini.

Good luck!