Cubase 5 has a savage array of routing for monitors, studio outs headphones and standard outputs. I was going to switch to another DAW because of the shite routing in previous versions but you can now even isolate the click to one or two outputs and even solo individual speakers in each output you have set up. all in software! basically you could have five different mixes running(using studio sends), and select which one you want down the cans.
Also punching in and out seems a lot easier and more accurate
sorry bit of a fanboy sounding digression but the options are so massive.