I would imagine you'll want to run the signal via the stereo analog outs of the UDP into the Cary, and then use the analog bypass on the Cary. In other words, using the DACs of the player should be superior to the Cary, but try it both ways and see. (If you use a digital connection, then you'd be using the DACs of the Cary instead of the player.)
Either way, nice gear!