I don't see it as a problem of CS, but management. It's a problem we've made all by ourselves.

Absolutely any problem involving humans where errors MUST be kept at ~0% in all cases (any you have just a bunch of variables that can combine and permute) becomes extremely hard.

If you add a ton of features to it, then it becomes intractable.

In my company, all meetings are set in GMT and a notification is sent as soon as the meeting is decided, which is never less than 3 days in advance. After that, it's not any software responsibility to attend to this meeting and it doesn't matter whether you received a reminder or not. You keep track of your local time. If your country decides to switch to the Mayan Calendar it's not my f*g problem, you keep track of GMT time. Period.