Hi jasondechert!
First, make sure that iTunes sees the device. When you click on the device it'll bring you to the device summary tab where it lists basic information about your device. You should see other tabs, one of which is entitled "Music."
Click on the Music tab and you'll presented with the following options:
1. Sync Music (with a checkbox)
2. All songs and playlists (with a radio box)
3. Selected playlists (with a radio box)
4. A listing of the playlists in iTunes (each with a checkbox)
5. Include music videos (with a checkbox)
Keep in mind that everything will be grayed out if you don't have the first checkbox (Sync music) checked. Once you check that first box you can then choose to sync all of your music (the entire library) or specific playlists. If you select "selected playlists" it will then allow you to choose the specific playlists you want to sync.
This URL should also help-
http://docs.info.apple.com/article.html?artnum=305741