First off, only one random event can trigger in a day. If you get an event at the house in the morning, you cannot randomly meet anyone else for the rest of the day. Repeat events blocking you? Rollback, quick save, quick load to avoid that event.
Second, the best way to trigger various events is to not let time pass, just exit and enter the location where your event should trigger.
Another option is to make a quick save before entering and reload if nothing happens. This is especially useful if you're trying to trigger specific morning events after sleeping.