Improved techniques to utilize and manage a group of media items (or media assets) on a computing device are disclosed. The group of media items can be utilized and managed at a host computer for the host computer as well as a media device (e.g., media player) that can couple to the host computer. One popular example of a group of media items is know as a playlist, which can pertain to a group of audio tracks. One aspect pertains to providing a persistent media device playlist at a host computer. Another aspect pertains to imposing capacity limits to a playlist, such as a media device playlist. Still another aspect pertains to a graphical user interface that enables a user to trade-off storage capacity of a media device between media asset storage and data storage. Yet still another aspect pertains to a graphical user interface that assists a user with selecting media items to fill a group of media items.