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.