Upgrade path from Windows laptop music server

Try Bluesound Node 2i into your Benchmark DAC. You will hear marked improvement in SQ. For best experience you will need an iPad to browse the content. 

Hello electroslacker!

First a couple of questions.
Is this a desktop system where you are just listening to headphones or are you feeding speakers as well ... and if so can you tell us more about the rest of your system.
And very importantly ... what is your budget?

Given that you are already feeding a Benchmark DAC, I do think it makes sense to upgrade your streaming source.

I'll throw out a couple of ideas at two very different price points both of which I have personal experience with.

(1) Would be to go the Bluesound route, pick up the current Bluesound Node 2i and connect to your Benchmark DAC via RCA terminated Coax cable.  The Blu OS interface is about as user friendly as you get (only thing that can truly beat it in my opinion is Roon).
This is my lower price thought.  Node 2i retails for $550, but can be had for less.  (I have 4 pieces of Bluesound kit in various rooms in my house including the Node 2i). 

(2)  Go the Roon route.  Roon Nuclues feeding your Benchmark directly via USB cable.  Nucleus is listed at $1399.  Roon subscription is $119 a year or $699 lifetime.   Nucleus has bay which can be fitted with HDD or SSD and function as your NAS if you so desire.  Roon interface is as good as it gets with either Tidal or Qobuz.  In today's world it is the gold standard.  In my main rig I have Roon Nucleus feeding Chord Qutest directly via USB, and all of my Bluesound pieces function as Roon endpoints. 

There are many other ways to skin this cat.  But these are two that I can highly recommend and have personal experience with.

PS.  Bluesound kit and Roon can both be controlled by PC, MAC, tablet, and/or smartphone including both Android and IOS devices.

@Jazzman7: Thx for info. To answer your questions:

It's the main system with floorstander speakers.  I have some headphones but rarely choose to use them.

The rest of the system is Benchmark DAC2 HGC running fixed output into a Modwright 36.5 linestage, into a VAC 200IQ tube amp to Sonist Concerto 4 Rev2 speakers. Interconnects are Benchmmark XLR.

As for price range, I don't mind paying for great sound quality. My amp and pre are used but "new" makes sense in a quickly evolving area like digital streaming.

I use a Node2i to a Benchmark DAC3B to McIntosh integrated to Joseph Audio Perspective  and get great sound. I have the Node hard wired and use an android tablet as a controller,  BluOS is very user friendly.  There are more expensive streamers but the Node is a great entry and I haven't  had the upgrade itch yet.