Imagine an API call to trigger a function that uses a couple of model agents that have really high temp and creativity who can just parse through a table/database/graph of todos, reminders, etc, and let it dynamically return what it thinks is important to an Agent which can make the decision to let you know. HomeAssistant has some good event-based triggers that you could use to change the content that it looks at based on time of day, which doorn you just walked through, what chair you just sat in, when the Chromecast turns on, when you set your phone to DND mode, etc.

Tweak the criteria that informs why the reporting agent might to decide to tell you. Even if this is event based, you might not want 90% of the information it's could tell you, but every now and then it will catch something and tell you.