Q: I just purchased a new 64GB iPad. My iTunes library has over 100 GB and I want to know how to only transfer a specified amount of music to the iPad, but in a random fashion—I dont want to pick and choose which artists, but just use a random playlist of say 5 GB.
A: Firstly if you’re using higher bit-rate music and you’re willing to live with 128kbps AAC files on your iPad, then you may want to simply choose the option to convert those files to 128kbps AAC, as explained in the question above.
If your music is already 128kbps AAC, or you want to use higher bit-rate music on your iPad, then you will need to use the option to sync selected playlists and create a playlist of your music. For selecting random tracks, a Smart Playlist is the best option. Simply create a playlist that selects a certain amount of music, say 5GB, based on Random selection:
Without any additional criteria, however, you’ll find that the random selection is relatively static—once the playlist is generated the content doesn’t change unless you manually refresh it or add some additional criteria to cause it to remove or refresh tracks automatically. For instance, adding a criteria to remove recently-played tracks would cause those to be taken out of the playlist and replaced with new, random tracks.
Other criteria could be used to refine this further, such as keeping high-rated tracks in your playlist regardless of whether you had listened to them recently or not, while removing recently-played lower-rated tracks.
You can also choose to create multiple Smart Playlists to select different types of music and sync each of these individually with your iPad, allowing you to more easily keep music of different genres and other criteria on your iPad. The above are just some examples to get you started—the possibilities are vast and a bit of experimentation with Smart Playlist criteria should easily allow you to find a good mix of settings to store a good selection of music on your iPad.