I use dBpoweramp for ripping and media monkey for playback. With Windows Vista, which I have, or a MAC you have no need for the ASIO driver anymore. That was a kernel mixer workaround for older versions of Windows.
A relatively cheap converter like the Hag or the Trends would turn you're non-USB DAC into a USB DAC so to speak. And theoretically this would be better than a direct coax connection to your computer's internal soundcard. Of course other much more expensive options, such as the above mentioned Apogee, also fit the bill.