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"Things on any given day has over 100 individual actions, most of which are recurring" looks more like checklist(s) to me.

There’s a reason pilots don’t use text files for their checklists. Sometimes people need better features.

Sure, but I would lose a ton of reminder and repeating action functionality.

I’d also have to scan across a dozen or more files to figure out what my day looks like.

Seems strictly worse to me.