What kind of laptop do you have?
1. Look into dBPoweramp. I've been using it more and feel like it's a much better program for ripping, playback and (especially) meta-data.
2. I usually prefer the toslink optical output of my MacBook Pro over USB. I know that some disagree, but this is my experience. If your computer doesn't have an optical output, then you will need a USB DAC or a USB to SPDIF adaptor. The best USB-SPDIF adaptor I have listened to is the HagUSB.
3. I use a variety of "glass optical" cables ranging from VanDenHul to custom built. As for USB cables, the cable that Hagerman includes with the HagUSB seems to be the best. Unlike some listeners, I can not tell a big difference in digital cables, and at times wonder if there is any difference.
The best thing I can recommend is to try different things out for yourself, and let you own ears and mind choose what's best for you. You have got the foundation right, which is ripping in a lossless format, and you have the right process in front of you, which is using a proper cable and DAC. The rest can be fun and very enjoyable. Just remember that it's about you and your music.
Hope this helps....
