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.