Winamp

Double-click on a playlist file to automatically load all the songs into Winamp. Also check your preferences.

Go to portables in your navigation pane, make sure your ipod is connected. Then click on your ipod, then in the bottom of you library pane for your ipod it will have the "sync" option. I myself dont like this way of doing it, so i just select the song/albums/artist that i want to add right click then hover your mouse over "send to" then find your ipod and bang only the songs YOU want go onto YOUR ipod.