Posted this in another thread, but since I just got my 3g Nano today, I think I have it figured out.
Download and install the latest Winamp free player. Download the install latest iPod Wimamp plugin from sourceforge. A pop-up will prompt you on which iPod you have--choose the right one. Fine-tune in preferences (i.e. which letter drive your iPod shows up in, etc.). Re-start your computer. Launch Winamp. Everything should work now.
Under the Media Library tab, click on "Devices", then "iPod". Open the folder with all your music from the playlist and you can add music from there. I just right-clicked the whole thing and sent it to the iPod. All the track/artist/album information loads up fine. That's how I do it, at least. I still use iTunes to encode AACs and open the finished folder from Winamp, but iTunes tends to get in the way now.