Timeline in Layers

Alright, I put together a sampler for this. 

Slide 1 is the broken one.

Layer 1:
The picture should change when the arrow starts fading. It's triggered by cue 1.
The picture should change again when the circle disappears. It's triggered by the circle leaving the slide. 

Layer 2:
No triggers. But none of my layers are allowing me to use Set Timeline to longest object.

Layer 3:
No triggers. Same timeline issue. Set timeline to default worked but, snapped some items on the main timeline back to the beginning when I did it. I fixed it, then did it again and it snapped them back again.

Main timeline:
The video visually vanishes before the sound. There's no animation on it and I don't see anything covering it, so I'm not sure what would cause that.

Slide 2 is working fine triggering actions based on layer cues. I can't see a difference between it and the first photo change on Layer 1.