Unfortunately, while I sometimes use Windows, I'm not much of a "geek" when it comes to using Windows (like I am with a Mac). Maybe someone else will know how...
This is my suggestion, if you want to put in some work now to have a better long-term solution.
Connect the iPod so that it appears in the iTunes sidebar, under DEVICES. Click the little triangle next to the iPod, so that you can see the iPod's playlists under the iPod. Right-click on the first one, and select Open in New Window. A separate window showing the playlist should open. Arrange and resize that window and the main iTunes window, so that you can see both.
In the main iTunes window, create a new playlist in your iTunes library. Name it like the playlist shown in the other window. From your main iTunes music library, drag songs to that new playlist to reproduce the playlist that's on the iPod. Hopefully, all of your songs on the iPod are in your iTunes library.
Repeat for every playlist on the iPod, so that your iTunes library has the same set of playlists that are currently on your iPod. You may want to begin these "On iPod" playlist names with an underscore or other symbol, so that they all appear grouped together in the iTunes sidebar where the playlist are shown.
Now, do a Restore of your iPod. When the Restore completes, select the iPod in the sidebar. Over to the right, go the Music tab. Set it up to automatically sync music, and select only those playlists you just created down below. When you Apply the change, your iPod should have those playlists and all the songs on those playlists.
Going forward, any change you make to those playlists will sync automatically to the iPod, whenever it is connected or you click the Sync button. You don't need to have the iPod connected to update those playlists. If you ever need to do a Restore again, it will be easy to sync the music back after the Restore. If you lose or break the iPod, you can get a new one and easily sync the same playlists to it.