You need a good soundcard on board the computer to do the A2D conversion if going out from the headphone jack. That is the main thing in regards to sound quality. I used this approach when I first started with computer audio and it can work pretty well. I have CDs I made off internet radio sources using this approach and they still sound pretty good.
Then I moved to Roku Soundbridge and recently Logitech Squeezebox network players with external DAC via wireless network connection. This is the way I would recommend ultimately assuming you have a Wifi network to start with.
Then I moved to Roku Soundbridge and recently Logitech Squeezebox network players with external DAC via wireless network connection. This is the way I would recommend ultimately assuming you have a Wifi network to start with.