Ten year old digital source upgrade suggestions?

It sounds like there is an issue with the rips.  It could be the Samsung, or (presumably iTunes) Apple software, or the interface between the two.  I don’t think is supporting iTunes, which is potentially another issue.
  There is software that improves iTunes and the accuracy of the rips.  You want accurate rips because presumably you may get rid of the CDs.  I mentioned dbPower Amp.  This program compares the quality of the data it’s reading to rips from other users.  It costs around $80.  I thought it gave audibly better rips than iTunes.  There is free software that others rate as equal called Exact Audio (I think-it’s been a few years) but there is advertising and I personally found it worked better with Windows than Macs.  Ymmv.  There may be others.
  I used The Apple  Optical reader for a few years. It made many errors with iTunes, a few with dbPowerAmp.  It did work a lot better than an expensive Bryston Optical Player which a total POS.

  My set up, with which I am very happy, is a Melco N100, and Melco D 100 for a ripper and CD transport.  The N100 feeds a SHM room correction device which uses Dirac Room Correction (the SHM also a streamer contained within, which I don’t use), and is connected to a Bryston DAC 3, which is a fantastic DAC.  My Oppo 105 Universal Disc player is also connected to the DAC via HDMI cable, and I use this to play SACD, since the Oppo can be programmed to output the DSD layer of SACD over HDMI, and I have a large Classical Music SACD collection.
  The Room Correction  and SACD may be a step to far for you at this point, so let’s drill down to ripper/streamer/DAC  issue for you.  A common solution for Audiophiles is the all in one Bluesound Vault.  I bought one years ago before I upgraded to Melco, and the Vault now resides in a HT system, which I am currently listening to as I type.  It costs around $1300.  It plays high resolution files.  It has a very good controlling App.  The weak points:1) not a perfect ripper-about the same level of error as the Apple 2) The DAC was not truly high end, although it is listenable and can be bypassedrecently upgraded the DAC, and I haven’t heard it, but people whose judgment I value say it isn’t that much of an improvement, and 3) Customer Service isn’t that good, and that is an issue that I am well acquainted with as it is prone to crashing and burning.
  The Melco N 100 can be used as a NAS (currently feeding my aforementioned Vault), but it is also a player and has an attached 2TB player.  I think it sounds amazing and works flawlessly.  Do you need the expensive Melco ripper?  No, but it’s accurate and also is superior to my Oppo as a CD transport.
  Other DACs that I have owned are PSAudio Digital Link III and Mytek Manhattan.  Both were excellent, but I really prefer the Bryston, which is great on detail but doesn’t sound overly Clinical and has the features (HDMI) that I want

Your weakest link is the USB cable. I can send you a long article on this; but check in with Used Cables.com. Be sure to get the right connectors on it. Shoot for a Wireworld Starlight Seven or equivalent. Don't get one much longer than you need. The "generic" one we use for computer printers are inadequate for music.

After borrowing an Audioquest Forest USB-A to micro and re-ripping two CD's I noticed a slight overall improvement over the previously ripped CD's.

While the player still sounds better the USB cable swap was a scary wake up call that has me waffling all over the place. All for the better, lots to learn. Thank you all.

M