PSA: edge cases I keep coming back to [v1]

I tried three different approaches and none of them felt quite right. Mostly thinking out loud — feel free to push back hard. Long-time lurker, first-time poster.

Maybe an unpopular opinion but here we go.

The trade-offs here are not obvious to me and I keep flip-flopping. Not sure if this is the right place to ask, mods please remove if it is not.