newbie ? on streaming internet audio to DAC

Rhyno..yes Winamp works just fine with outboard DACs. Use Winamp as your primary internet radio player.There are so many options or ways to to do this it is mind boggling.
You can go SB3 or use a similar wireless device or you can go through a USB converter to DAC or USB DAC.

Rhyno - A direct connection from the headphone out on your pc to your stereo is the easiest and least expensive way to go

a usb dac is the next easiest option and will offer a huge improvement in quality. www.firestone-audio.com has one for $120, there are many others at various prices to choose from.

an airport express from apple will add wireless with a digital or analog out for $99 and can be relatively simple to set up

a squeezebox (SB3) is a bit more difficult than the airport express to set up but adds the ability to browse your music and select Internet radio stations via a remote control for $300. It can also connect to a wireless network and play Internet radio without a host computer, a great feature.

Good luck!