Hi charliemason,
If you turn the AutoDJ off and then back on again just in time for the scheduled playlist it may work, but you are better off just leaving it to do this naturally as it will disrupt your listeners and you may miss the scheduled playlists start time. The best way would be to build you playlists with this in mind, so keep an eye on their total running time. So for example, try and keep each playlists total time length as close to an hour as you can. Even with a matter of seconds over or under an hour for each it will still keep things pretty much on schedule.