And also, how can I use the Apple Remote app? It's crashing and won't connect to iTunes.
You can download an application from this website to do this.
After downloading, make sure your iPod is plugged in and iTunes is not open. If the application does not recognize your iPod, it will give you a link to a page that should have a solution (though you probably won't have this problem).
You can select a folder to put your iPod music in or create a new one. If you would like to put all your music into the folder use ctrl A to select all the songs in the list. Otherwise, you can select one song at a time, or hold down ctrl and click on each song.
Once your music has finished transferring, you can play it in the application of your choice.