DAC to match $2-3K CD player

Listened to the Rolling Stones' Beggars Banquet last night--first streaming Apple Lossless files via Squeezebox Duet, then on my Naim CD5x. Of course, with the bare Squeezebox and no external DAC, there was no comparison. What I'm wondering is how far up the DAC food chain would you need to start looking to match the sound quality of a $2-3K dedicated player? (I tried a Musical Fidelity V-DAC in my office and was unimpressed, so I'm not looking for a giant killer.) I'm not going all digital any time soon, so my question is really out of curiosity and to start a conversation if anyone else is interested.
I don't know anything about the Monarchy Audio NM24, Clio09, will have to check it out.

Is the modded PS Audio DL3 a different beast, Jimhsu? In what way? I ask because a friend bought the stock model to replace a Cambridge Audio Dacmagic and ended up going back to the Dacmagic; he thought it was too smooth and not as dynamic as the Dacmagic. (My sense of the Dacmagic is that, while it would improve the Squeezebox, it can't compare with the CD5x.)

The W4S DAC-1 sounds very interesting. It gets at the idea behind my question: that a $1000-1500 DAC might give a $2-3K cd player a run for its money--and offer more flexibility to boot. I'm curious, Smholl, is the presentation similar to the CD5x?
We have the Wyred for Sound Dac 2, listened on the weekend to a nearly decade old Classe CDP 1.5 and a brand new Arcam CD 17. Dac 2 through Squeezebox was the best sounding by a very small margin. It's a bit more up front in it's presentation compared to the Classe which is very smooth sounding. Mind you the Dac 2 has only about 50 hours on it thus far. We are liking it very, very much!
Afranta- W4S DAC-1 has more detail (don't take that as harsh, etchy)and bass is more solid. CD5x tended to call attention to some parts of the audio spectrum, while seeming to attenuate others. Not knocking the CD5x, I had it for about 2 years and enjoyed the sound.
But as I started to get more and more into ripping CD's and purchased the DAC-1 to go with the Duet, I was using the CD5X less. I enjoyed the ripped CD going through the Duet/DAC-1 more than listening to the same CD through the CD5x. Just a matter of preference I suppose.
Smholl, I have read your comments with great interest. What is the rest of your system? Thanks.
Thanks, Smholl (and Audiowoman). I've begun ripping my cds, and your description of the W4S dac makes me think that maybe I'm closer to going that route than I thought ...