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The two hard parts of a repeating deadline
"Repeats monthly" looks like an afternoon of work and turns into a week. The two edges where recurrence breaks, and how to build it so the dates hold.
I built a sandcastle, then I designed the wave
Half of making something is building it. The other half is deliberately designing the forces that try to break it, because you can't trust what you haven't tried to break.
The floor and the ceiling
A per-deadline reminder and the overview you open answer two different questions, so a tool that does its job needs both, the push that finds you and the pull that shows you everything at once.
One surface, no hidden settings
Simplicity is not the absence of capability but the refusal to make the user hunt for it, so a control belongs where the user already reaches for it, not scattered behind menus.
It is hard to go back and forth. That is the work.
Usefulness comes from the unglamorous willingness to revisit decisions you thought were settled, and the back-and-forth that feels like backtracking is actually the work.