Importance of Ripping CD to My Music Server

Over the years my system has evolved to a pretty decent system that sounds fabulous.  My system currently consists of:
  • McIntosh C2600 Tube Preamp
  • McIntosh MC452 Amp
  • Martin Logan Montis Speakers
  • Sony HAP Z1ES Audio Server
  • Pro-Ject Debut Carbon turntable (don't use it much)
  • Acoustically treated listening room
I enjoy listening to music from my Sony high resolution file player 99% of the time.  I like the convenience and I don't have a great turntable or big selection of vinyl so my server works best for me.  

I currently RIP CD's to my hard drive on my Personal Computer then transfer them to my Sony.  I use Loss Less FLAC files.

My question:  Am I missing music quality by using the process I describe above?  If so, is possible to quantify how much better my listening experience would be by using another process?

I feel like that part of the process is worth exploring next.  I am happy with my electronics, my speakers, and recent improvements to acoustic treatments in the room.

00cac13c 9c60 4861 af58 21ff08dcbc8fbikerneil
No and no telling. Ripping is pretty much data.
It’s how you play it that makes the music.

dbPoweramp check.
Sony S590 and Rip Script check.
NAS retired.
4 of 5 players pass native DSD.
Just for the heck of it, you might try an external DAC and see if it makes a difference...

I always wonder about internally upscaling/upsampling from PCM to DSD...  I'm not a fan...

When you RIP to FLAC aren’t you in PCM? And then the HAP Z1ES upscales/upsamples/converts to DSD...