Don't think you are ever going to be able to use your Nano for a remote... Its a fine device for what it is but... it doesn't have a digital out; it doesn't have the capacity to store any significant amount of non-lossy compressed music; it doesn't have bluetooth; and, even if it had bluetooth, bluetooth doesn't have the over the air capacity to do a digital audio PCM stream.
If you want an iPod interface, maybe the Squeezebox is for you. Gives you a remote and the Squeezebox interface is sort of like the control on the iPods. You can use the digital output of the squeezebox and run that into a standalone DAC for pretty good quality playback. Plus, with a bit of messing around, you can get the slimserver software that the squeezebox uses to "sync" with your iTunes music library, so you are only modding the library with one program....
If you want an iPod interface, maybe the Squeezebox is for you. Gives you a remote and the Squeezebox interface is sort of like the control on the iPods. You can use the digital output of the squeezebox and run that into a standalone DAC for pretty good quality playback. Plus, with a bit of messing around, you can get the slimserver software that the squeezebox uses to "sync" with your iTunes music library, so you are only modding the library with one program....