Reminder that edge cases after a year [v3]

The trade-offs here are not obvious to me and I keep flip-flopping. I tried three different approaches and none of them felt quite right. Mostly thinking out loud — feel free to push back hard.

Not sure if this is the right place to ask, mods please remove if it is not. Maybe an unpopular opinion but here we go. Mostly thinking out loud — feel free to push back hard.