iTunes is a PITN, so I only use it when there isn't a good dedicated app (or I'm going to run out of time before I run out of book on OverDrive). I get around the playlist issue by noting if I'm likely hit the end of a book before the end of my commute, and either I make a point of finishing it in odd moments before the drive, or if it'll last most of the trip, just switch to the news at the end. The low-tech solution.
I don't know what you like to listen to, but my listens tend to be longish so it's not a major issue.