[jaggrey]

It won't show two upcoming items if they occur within the same time frame (conflicting appointments). In my experience, it'll show 1 all-day appointment (regardless of how many are there), the current or next upcoming appointment, and the one after that (if it's within a few hours), all simultaneously. If you have an appointment that's conflicting, it won't show the conflicting appointment until it starts; it won't show it as upcoming.

Confused yet? lol