If you think calendar apps are a pain try television broadcast automation... frame accuracy instead of per second, with fractional frame rates (29.97, 23.98, fps) and a mix of content of different frame rates on the same playlist and conversion to different frame rate on the way out, plus operators in a different timezone than the channel and the need to handle timezone changes without messing things up on air.

I have nothing to do with it but this is an open source automation project I have bookmarked with some of those functions:

https://github.com/jaskie/PlayoutAutomation/blob/develop/TAS...

Lots of hassles.