A lot of open gaps to really know what happened here. 10 years ago I sold my Classe $3000 CD player which was rated very high because my ripped music sounded better. So if you are saying that a cheaper CD player sounds better, something doesn't jive.
You didn't state how you were reading the ripped music, did you use iTunes? If so, that's part of the problem, If you use pure music or especially Audirvana having these programs reading your music files, there is no way your CD player can sound better.
How did you hook your Mac to the dac? USB? That could be your other issue. How did you rip your music? iTunes? MAX? XLD? If you used iTunes, all bets are off.
I went the 3rd party music server route about 4 years ago using the Auralic Aries hooked up using the AQ Diamond usb cable to an external dac running with their DS Lightning software. At the time, thought it sounded better than the Lunins and Aurenders I auditioned.
Almost 3 years ago, I dumped everything USB, got rid of the music server that was in my audio room, and went with Roon running on a dedicated Mac mini hooked up using ethernet to a ps audio DS sr dac. Hands down, much better than the prior setups. I have done different tests using a sacd/CD player and the network connection sounds the best.
Keep it simple with high SQ returns