Hi HPDJ! It would be interesting to know what CD player that is you are talking about, as it is basically what you would be upgrading from. here is my experience: I used to listen to a tube output Cayin 15T (with switchable upsampling), which I had bought new for about 1500$ Can$ (just so you have an idea). I built my own DAC (a kit from audionote:2000$, much more expensive if you go for the finished product). I have 1000 CD's stacked away in drawers and lying all over the place in piles. I was miserable for years, never finding what i wanted to listen to, searching for ever, ending up listening to the same 20 CD's that I kept in a pile near my cd player.
A few months ago i decided to move away from this unbearable lifestyle, bought a 100$ 2Tb external drive and started ripping my CD's to flac via EAC (in case one of them explodes or goes into internal combustion/atomic fusion, you need to have a backup of all your music).
Then I installed a usb port on my DIY DAC (a diy hagerman usb port). The HAG came highly recommended, yet it sounded like crap.
I tried to understand what the best wifi solution was for relaying data from PC to DAC, but the information was enragingly inconsistent (or else there is always a perfect solution for 5000$).
I decided to go with a cheap USB cable from Staples. (50$, 5 meters).
I could not listen to the hagerman so I continued listening to my CD player.
Then I discovered the Musical Fidelity V-link 192. The V link is a usb to spdif converter. (I know, this sounds like a commercial)

Got one for about 400$ from germany (via ebay) and TADA!
My CD player is now gathering dust, because the sound was simply MUCH better, visibly and audibly so, from the very start. I have no idea why, presumably lack of jitter??? (at this point I was using the cd player as a transport, of course, since I have the AN DAC).
My PC runs all day, so I don't have to turn it on for music listening. It happens to be in an adjacent room, so I don't need to make it more silent than it is (it is also DIY, with a wooden case ). A long cable running through the hallway is the biggest disadvantage of this setup.
I don't even need the wifi to be on, unless I need to remote control the PC through my Ipod. I use Foobar (freeware), which plays flac files (and everything else) using ASIO 64 drivers (easily installed).
I am not a fan of physical CDs, or booklets, although I read them all when I get a chance.
I tried to make a diy usb cable, but couldn't find diy usb plugs. Information on usb cable impact on sound quality is also enragingly inconsistent. But I can tell you that my 50$ cable, whether it is the bottleneck or not, runs circles around the CD player.
For me this was the way to go and i can't imagine going back. I am not attached to the Cd player, I was born in 74 and the advent of Cds forced me to stop attaching myself to media. It was sad enough to lose the tapes, i wouldn't let technology hurt me again

If you need specific help just let me know
PS: moving up from my CD'S internal DAC to the external DAC was the biggest move forward in terms of sonic experience. Followed by the replacement of the CD transport with the PC as a transport. But the convenience of being able to play any album i feel like!!!!!!!!!!!! Oh boy!!!!!!!!!!