Upgrade path from Windows laptop music server

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.

@sebrof

@Jazzman7: In your #1 / Bluesound route, where would electroslacker store his music files? Or is that option only for streaming, no files?

Any network share would work.
My first NAS was simply an external hard drive plugged into my router.
Eventually I graduated to a Melco N1A.

@electroslacker

Should be no need to re-rip your music files.  Just a matter of them being located somewhere that is discoverable on your network and then pointing/defining that location to your streamer be it Bluesound device, Roon Nucleus, or whatever else you may decide on.  Moving your music files from one network location to another is just a matter of copying your files over, which can be as simple as drag and drop.

And just out of curiosity.  How much music do you have, and how have you stored it.
I myself rip everything as uncompressed Flacs using dBpoweramp.