Q: I have bought some audiobooks from eMusic which are provided as hundreds of three-minute files, with titles numbered 001 through 233 (for example). How can I organize these in iTunes and on my iPod to facilitate playback without having to keep track of which segment I am on? Is there any way to set up a playlist that will remember my place in the sequence of files, in the same way that the “Remember playback position” will remember my place within an individual file?
– Joe

A: Although neither iTunes nor the iPod can remember your position within a playlist, they do keep track of which items you’ve listened to by setting a “Last Played Date” and “Play Count” for each item as you listen to it.
Therefore, the easiest way to solve this problem is through the use of Smart Playlists to track which audio book chapters you’ve already listened to and thereby remove them from the playlist as you listen to them.
You can either start by placing all of your audiobook tracks into a standard playlist, or if they are properly tagged simply build the Smart Playlist to identify and group all of those tracks by the audiobook title, album, or artist fields.
You would then specify a criteria of “Play Count” is 0 to only include those sections that you had not listened to. For example, the following Smart Playlist would select all of the chapters/tracks in a specific audiobook, excluding those that have already been played through to the end:
You would then ensure this playlist is synced to your iPod, and listen to your audiobook tracks directly from this playlist.