Autoplay after crossfade & audio channel

I'm a complete noob about DJ sw, but this Sunday I did need to manage video&audio mix for a live event in a theater (a NPO acting as ballet school).
My need are pretty simple: playlist, manual control of the next video/audio to be played, manual crossfade when needed in the middle of some song/clip.
Here my question: when I did push the Auto crossfade triangle work as expected, except I can't make it play the second item automatically. Any hint?
Also I did have a specific need: in one element I need to switch between two videos, but leaving the same song in play. Any way to achieve that?
My need are pretty simple: playlist, manual control of the next video/audio to be played, manual crossfade when needed in the middle of some song/clip.
Here my question: when I did push the Auto crossfade triangle work as expected, except I can't make it play the second item automatically. Any hint?
Also I did have a specific need: in one element I need to switch between two videos, but leaving the same song in play. Any way to achieve that?