#1: Optical and HDMI will have identical results for audio quality for anything you'll be playing back that is not a ripped bluray. (HDMI can bitstream the HD audio formats that optical cannot, though this should yield no actual quality difference, it would just require your computer to do more processing). If you go with an analog signal quality can vary widely, which brings me to...
#2: Most, if not all, video cards with HDMI or sound cards with optical will allow you to send the signal completely unmolested to your receiver which will then do the 'processing.' If you choose to go with an analog connection (which i would highly recommend against) the quality of sound from better sound cards will be better.
Tip for success: When using a computer for audio it's important to set the 'default format' to whatever bit/sample rate your recording is using. For CD audio this is 16 bit 44.1khz. If this is set to something else the computer will resample the audio which negatively impacts the quality.