After trial and error I've come up with a method on how to choose songs for your devices and how to organize them. Everyone has their own methods so feel free to share yours. What songs/tracks to Not sync: - Don't sync songs that you think may come in handy in a certain situation some day. Chances are this day won't come. (for example don't have the monster mash on your device all year because you may need it on Halloween) - Don't sync songs that you think others may like. Unless you use your device to DJ assume you will be the one listening to these songs. - Don't sync songs that have you reaching for the "next track" button within 20 seconds. You'd be surprised how much time is spent skipping songs on your commute to school/work. - Don't sync songs you wouldn't be able to listen to 2 times in a row. (my songs are so fine tuned that I could listen to the same song 3 times in a row and not mind). How to Organize your music: Mood/Emotion: All songs have an emotion to them. They can be angry, sad, upbeat, inspirational. As a general rule I keep similar "emotion" songs together otherwise you end up on a rollercoaster ride of emotions. (Imagine an angry Metal song followed by a Lionel Richie song.) Genre: This is a no brainer. Rock songs, Rap songs, Dance songs. Feel free to share how you organize your songs.