Is FlyingVehicle<T> implement for LocalPlane with any <T> besides LocalController? You can only go from Box<LocalPlane> to Box<dyn FlyingVehicle<T>> if LocalPlane implements FlyingVehicle<T>.
More generally I suspect some confusion between generics and dyn Trait, but I'm not completely sure, and it's unclear to me why you have the specific function signatures that you do. dyn Trait is a concrete type, despite being dynamically sized and dispatched.
The compiler supplies an implementation of Trait for dyn Trait, but not for other types, so you can supply implementations like
impl Controller for Box<dyn Controller + '_> {}
impl Controller for Box<dyn Controller + Send + '_> {}
impl Controller for Box<dyn Controller + Send + Sync + '_> {}
but that still won't make dynamic_function callable unless LocalPlane implements FlyingVehicle<Box<dyn Controller>>.
And doesn't require Box<Controller + '_>: Controller (though you probably want those anyway) and doesn't lead to making three variants for the + Send + Sync like cases.